Alkenylimidazoles: methods of synthesis and chemical properties

O. Ya. Mel’nik, V. O. Chornous, A. M. Grozav, M. V. Vovk

Abstract


The aim of this review was to summarize and systematize literature on chemistry of alkenylsubstituted imidazoles known as important synthetic substrates and precursors for the synthesis of biologically active substances. Two approaches to the synthesis of these compounds are reviewed: 1) the imidazole ring formation based on functionalized alkenyl compounds; 2) functionalization of imidazole derivatives with the alkenyl moiety. The second approach prevails and includes condensation of methylimidazoles with carbonyl compounds, reactions of formylimidazoles with compounds containing activated methylene groups and phosphorus ylides, as well as reactions of dehydration and dehydrohalogenation of substituted imidazoles. The methods of synthesis of alkenylsubstituted imidazoles have been analyzed in detail; their synthetic potential and limits have been described. Special attention is paid to the authors’ own research on the synthesis of new 4-chloro-5-alkenylsubstituted imidazoles using 5-formylimidazoles as precursors. Analysis of the chemical properties of alkenylsubstituted imidazoles has allowed conducting their strict classification and systematizing their typical transformations. Reactions of cyclocondensation are the first ones to be mentioned, they proceed through the interaction of the alkenyl moiety with another functional group or endocyclic Nitrogen. Other transformations such as heterocyclofunctionalization, oxidation and reduction are based on transformation of the alkenyl moiety. It should be noted that heterocyclization processes are new for chemistry of alkenylimidazoles, they are successfully applied to 5-(2-nitro-alkenyl)- and 5-(2-arylvinyl)substituted derivatives, and due to them it is possible to obtain new promising hybrid structures.

Keywords


alkenylimidazoles; synthesis methods; condensation; chemical properties; heterocyclofunctionalization

References


Fromtling, R. A. (1988). Overview of medically important antifungal azole derivatives. Clinical Microbiology Reviews, 1 (2), 187–217. doi: 10.1128/CMR.1.2.187

Sharpe, T. R., Cherkofsky, S. C., Hewes, W. E. et al. (1985). Preparation and antiarthritic and analgesic activity of 4,5–diaryl–2–(substituted thio)–1H–imidazoles and their sulfoxides and sulfones. Journal of Medicinall Chemistry, 28 (9), 1188–1194. doi: 10.1021/jm00147a011

Ucucu, U., Karaburun, N. G., Isikdag, I.(2001). Synthesis and analgesic activity of some 1–benzyl–2–substituted–4,5–diphenyl–1H–imidazole derivatives. Il Farmaco, 56 (4), 285–290. doi: 10.1016/S0014–827X(01)01076–X

Graczyk, P. P., Khan, A., Bhatia, G. S. et al. (2005). The neuroprotective action of JNK3 inhibitors based on the 6,7–dihydro–5H–pyrrolo[1,2–a]imidazole scaffold. Bioorganic & Medicinal Chemistry Letters, 15 (21), 4666–4670. doi: 10.1016/j.bmcl.2005.07.076

Laufer, S. A., Zimmermann, W., Ruff, K. J. (2004). Tetrasubstituted imidazole inhibitors of cytokine release: probing substituents in the N–1 position. Journal of Medicinall Chemistry, 47 (25), 6311–6325. doi: 10.1021/jm0496584

Black, J. W., Durant, G. J., Emmett, J. C. (1974). Sulphur–methylene isosterism in the developent of metiamide, a new histamine H2–receptor antagonist. Nature, 248 (5443), 65–67. doi: 10.1038/248065a0

Jin, Z. (2009). Muscarine, imidazole, oxazole and thiazole alkaloids. Natural Product Reports, 26 (3), 382–445. doi: 10.1039/B718045B

Jin, Z. (2006). Imidazole, oxazole and thiazole alkaloids. Natural Product Reports, 23 (3), 464–498. doi: 10.1039/B502166A

Jin, Z. (2005). Muscarine, imidazole, oxazole and thiazole alkaloids. Natural Product Reports, 22 (2), 196–229. doi: 10.1039/B316104H

Cui, B., Zheng, B. L., He, K. et al. (2003). Imidazole alkaloids from lepidium meyenii. Journal of Natural Products, 66 (8), 1101–1103. doi: 10.1021/np030031i

Grimmett, M. R. (1997). Imidazole and benzimidazole synthesis.London: Academic Press., 265.

Katritzki, A. R., Rees, C. W. (1997). Comprehensive heterocyclic chemistry. Elsevier Science Ltd, 5, 994.

Kyrides, L. P., Zienty, F. R., Steahly, G. W. et al. (1947). Substituted imidazoles and 2–imidazolines. The Journal of Organic Chemistry, 12 (4), 557–586. doi: 10.1021/jo01168a015

Cappon, J. J., Witters, K. D., Baart, J. et al. (1994). Synthesis of L–histidine specifically labelled with stable isotopes. Recueil des Travaux Chimique des Pays–Bas. 113 (6), 318–328. doi: 10.1002/recl.19941130603

Olson, G. L., Cheung, H.–C., Chiang, E. et al. (1995). Peptide mimetics of thyrotropin–releasing hormone based on a cyclohexaneframework design, synthesis, and cognition–enhancing properties. Journal of Medicinall Chemistry, 38 (15), 2866–2879. doi: 10.1021/jm00015a009

Kuwano, E., Takeya, R., Eto, M. (1989). Pat. US4812473 A. 1,5–Disubstituted imidazoles as inhibitors of juvenile hormone. declared 24.03.1987; published 14.03.1989.

Arbonés, C., Sánchez, F. J., Marco, M.–P. et al. (1990). Fluorinated analogues of the imidazole insect growth regulator KK–42. Heterocycles, 31 (1), 67–78. doi: 10.3987/COM–89–5125

Shafiee, A., Rastkary, N., Foroumadi, A. (1998). Syntheses of 2–(2–arylethyl)imidazoles. Journal of Heterocyclic Chemistry, 35 (3), 607–610. doi: 10.1002/jhet.5570350319

Henry, D.W., Brown, V. H., Cory, M. et al. (1973). Chemotherapeutic nitroheterocycles. Antischistosomal properties of nitrofurylvinyl and nitrothienylvinyl heterocycles. Journal of Medicinall Chemistry, 16 (11), 1287–1291. doi: 10.1021/jm00269a015

Henry, D. W., Cory, M. (1976). Pat. US3993643. A N–substituted 2–[2–(5–nitro–2–furyl)vinyl]imidazoles. declared 07.05.1976; published 23.11.1976.

DeBernardis, J. F., Gifford, P., Rizk, M. et al. (1988). Evaluation of the side arm of (naphthylvinyl)pyridinium inhibitors of choline acetyltransferase. Journal of Medicinall Chemistry, 31 (1), 117–121. doi: 10.1021/jm00396a017

Suwiriski, J., Swierczek, K. (1993). Nitroimidazoles XVII. Nucleophilic amination or ring transformation in reactions of l–aryl–4–nitroimidazoles with 4–amino–1,2,4–triazole or hydroxylamine. Tetrahedron, 49 (24), 5339–5350. doi: 10.1016/S0040–4020(01)82383–8

Allsebrook, W. E., Gulland, J. M., Story, L. F. (1942). The constitution of purine nucleosides. Part X. A new synthesis of xanthine and attempted syntheses of xanthine glucosides from glyoxalines. Journal of the Chemical Society, 232–236. doi: 10.1039/JR9420000232

Baddiley, J., Buchanan, J. G., Hardy, F. E. (1959). Chemical studies in the biosynthesis of purine nucleotides. Part 111. The synthesis of 5–amino–l–(β–D–ribofuranosyl)glyoxaline–4–carboxyamide and 4–amino–l–(β–D–ribofuranosyl)glyoxaline–5–carboxyamide. Journal of the Chemical Society, 2893–2901. doi: 10.1039/JR9590002893

Tantravedi, S., Chakraborty, S., Shah, N. H. et al. (2013). Analogs of iso–azepinomycin as potential transition–state analog inhibitors ofguanase: synthesis, biochemical screening, and structure–activity correlations ofvarious selectively substituted imidazo[4,5–e][1,4]diazepines. Bioorganic & Medicinal Chemistry Letters, 21 (17), 4893–4903. doi: 10.1016/j.bmc.2013.06.069

Giraldi, P. N., Mariotti, V., De Carneri, I.(1968). Antiprotozoans. Synthesis and biological activity of some styrylimidazole derivatives. Journal of Medicinall Chemistry, 11 (1), 66–70. doi: 10.1021/jm00307a014

Chan, E., Putt, S. R., Showalter, H. D. H. et al. (1982). Total synthesis of (8R)–3–(2–deoxy–β–D–erythro–pentofuranosyl)–3,6,7,8–tetrahydroimidazo[4,5–d][1,3]diazepin–8–ol (pentostatin), the potent inhibitor of adenosine deaminase. The Journal of Organic Chemistry, 47 (18), 3457–3464. doi: 10.1021/jo00139a015

Asato, G., Berkelhammer, G. (1972). Nitroheterocyclic antimicrobial agents. 1–Methyl–2–nitro–5–imidazolyl derivatives. Journal of Medicinall Chemistry, 15 (10), 1086–1088. doi: 10.1021/jm00280a030

Cavalleri, B., Ballotta, R., Lancini, G.C. (1972). Synthesis of 1–alkyl–2–nitroimidazole–5–carboxaldehydes. Journal of Heterocyclic Chemistr, 9 (5), 979–984. doi: 10.1002/jhet.5570090502

Cavalleri, B., Ballotta, R., Arioli, V. et al. (1973). New 5–substituted 1–alkyl–2–nitroimidazoles. Journal of Medicinall Chemistry, 16 (5), 557–560. doi: 10.1021/jm00263a035

Cavalleri, B., Volpe, G., Arioli, V. (1977). Synthesis and biological activity of some vinyl–substituted 2–nitroimidazoles. Journal of Medicinall Chemistry, 20 (5), 656–660. doi: 10.1021/jm00215a007

Burnett, F. N., Hosmane, R. S. (2002). Synthesis of a novel ring–expanded purine analogue containing a5:8–fused imidazo[4,5–e][1,2,4]triazocine ring system amidstopportunistic rearrangements and ring transformations. Tetrahedron, 58 (47), 9567–9578. doi: 10.1016/S0040–4020(02)01252–8

Hosmane, R.S. Bhan, A. , Rauser, M. E. (1985). Facile conversion of 4(5)–nitro–5(4)–methylimidazoles into4(5)–nitro–5(4)–cyanoimidazoles. The Journal of Organic Chemistry, 50 (26), 5892–5895. doi: 10.1021/jo9824910

Burnett, F. N., Hosmane, R. S. (1997). Imidazo[4,5–e][1,2,4]triazocine: a novel 5:8–fused ring system riddled with rearrangements. Heterocyclic Communications, 45 (5), 857–861. doi: 10.3987/COM–97–7783

Ross, W. J., Todd, A. (1973). Antiparasitic nitroimidazoles. 7. Some 4– and5–styrylnitroimidazoles. Journal of Medicinall Chemistry, 16 (7), 863–865. doi: 10.1021/jm00265a030

Burnett, F. N., Hosmane, R. S. (1995). Synthetic approaches to 5:8–fused heterocyclic systems. A novel rearrangement during the synthesis of imidazo[4,5–e][1,2,4]triazocine ring system. Nucleosides & Nucleotides, 14 (3–5), 325–328. doi: 10.1080/15257779508012373

Siddiqui, S., Hosmane, R. S. (2000). Synthetic analogue of stilbene containing an imidazole nucleus. Molecules, 5 (6), 856–863. doi: 10.3390/50600856

Alcalde, E. , Roca, T. , Fayet, J. P. et al. (1991). Aza–analogs of stilbene with a dipolar character. (E)–1–alkyl–(2–(azolyl–2–idene)etylidene)–dihydropyridines and (E)–2–(2–(1–alkyl–3–pyridinium)vinyl)azolate inner salts. Chemistry Letters, 20 (12), 2151–2154. doi: 10.1246/cl.1991.2151

Alcalde, E., Roca, T. (1992). Heterocyclic betaines. 14. (E)–l–Alkyl–[2–(imidazol–2–ylidene)ethylidene]dihydropyridines with a betaine character. An improved protocol for a Knoevenagel–type condensation for synthesis of(E)–l–alkyl–[2–(1H–imidazol–2–yl)vinyl]pyridinium salts. European Journal of Organic Chemistry, 57 (18), 4834–4838. doi: 10.1021/jo00044a015

Fichera, M., Fortuna, C.G., Impallomeni, G. et al. (2002). Studies on the interactions of the new 2,6–bis[2–(heteroaryl)vinyl]–1–methylpyridinium cations with the decamer d(CGTACGTACG)2. The Journal of Organic Chemistry, 2002 (1), 145–150. doi: 10.1002/1099–0690(20021)2002

Adamo, M. F. A., Duffy, E. F. , Konda, V. R. et al. (2007). An improved synthesis of 3–methyl–4–nitro–5–heteroarylethenylisoxazoles. Heterocycles, 71 (5), 1173 – 1181. doi: 10.3987/COM–07–11023

Karjalainen, A. J., Kangas, L. V. M., Kurkela, K. O. A. (1992). Pat. US5098923 A. Aromatase inhibiting 4(5)–imidazoles. declared 27.09.1990; published 24.03.1992.

McNab, H., Thornley, C. (1997). New synthetic routes to pyrrolo–[1,2–a]– and –[1,2–c]–imidazol–5–ones by flash vacuum pyrolysis. Journal of the Chemical Society, Perkin Transactions 1, 15, 2203–2209. doi: 10.1039/A701751K

Crozet, M. D., Suspеne, C., Kaafarani, M. et al. (2004). Synthesis of a new imidazo[4,5–b]pyridin–5–one via a vicarious nucleophilic substitution of hydrogen Heterocyclic Communications, 63 (7), 1629–1635. doi: 10.3987/COM–04–10069

Keenan, R. M., Weinstock, J., Finkelstein, J. A. et al. (1993). Potent nonpeptfde angiotensin II receptor antagoqists. 2. 1–(Carboxybenzyl)imidazole–5–acrylic acids. Journal of Medicinal Chemistry, 36, 1880–1892. doi: 10.1021/jm00065a011

Karjalainen, A., Kalapudas, A., Sodervall, M. et al. (2000). Synthesis of new potent and selective aromatase inhibitors based on long–chained diarylalkylimidazole and diarylalkyltriazole molecule skeletons. European Journal Pharmaceutical Sciences, 11 (7), 109–131. doi: 10.1016/S0928–0987(00)00074–9

Ono, M., Hori, M., Haratake, M. et al. (2007). Structure–activity relationship of chalcones and related derivatives as ligands for detecting of β–amyloid plaques in the brain. Bioorganic & Medicinal Chemistry, 15, 6388–6396. doi: 10.1016/j.bmc.2007.06.055

Nakayama, M., Haratake, M., Ono, M. (2009). Pat. EP2030635 A1. Composition for diagnosing amyloid–related disease. declared 22.05.2007; published 04.03.2009.

Shioiri, N., Mikami, T., Morimoto, S. et al. (2000). Pat. US6071943 A. Іmidazole derivative and medicinecomprising the same as activeingredient. declared 30.11.98; published 06.06.00.

Omar, A. M., Mahran, M. A., Ghatge, M. S. et al. (2015). Identification of a novel class of covalent modifiersof hemoglobin as potential antisickling agents. Organic & Biomolecular Chemistry, 13 (22), 6353–6370. doi: 10.1039/c5ob00367a

Selvakumar, N., Kumar, G. S., Azhagan, A. M. et al. (2007). Synthesis, SAR and antibacterial studies on novel chalcone oxazolidinone hybrids. European Journal of Medicinal Chemistry, 42 (4), 538–543. doi: 10.1016/j.ejmech.2006.10.013

Chornous, V. A., Melnik, O. Ya., Hrozav, A. N. et al. (2014). Zhurnal orhanichnoi ta farmatcevtychnoi khimii – Journal of Organic and Pharmaceutical Chemistry, 12 (3), 28–32.

Chornous, V. A., Grozav, A. N., Melnik, O. Ya. et al. (2015). Polyfunctional imidazoles: X. Synthesis of 4–chloro–5–(2–nitroalkenyl)–1H–imidazoles and their reaction with 5–methyl–2,4–dihydro–3H–pyrazol–3–one. Russian Journal Organic Chemistry, 51 (4), 251–257. doi: 10.1134/S1070428015040132

Chornous, V. A., Melnik, O. Ya., Kutsyk, R. V., Vovk, M. V. (2014). Nauk. visnyk Chernivetskoho universytetu, 683. „Khimiia”. Chernivtsi: Chernivetskyi natsionalnyi universytet, 90–96.

Chornous, V. A., Melnik, O. Ya., Hliebov, O.M. et al. (2016). Zhurnal orhanichnoi ta farmatcevtychnoi khimii – Journal of Organic and Pharmaceutical Chemistry, 14 (1), 46–52.

Melnik, O. Ya., Melnik, D. A., Chornous, V. A., Melnichenko, N. V., Vovk, M. V. (2016). Visnyk Lvivskoho universytetu. Seriia khimichna, 57 (2), 280–285.

Kokosa, J. M., Szafasz, R. A., Tagupa, E. (1983). Practical multigram synthesis for 4(5)–vinylimidazole. The Journal of Organic Chemistry, 43 (20), 3605–3607. doi: 10.1021/jo00168a062

Cheng, J.–F., Chen, M., Liu, B., Hou, Z. et al. (2006). Design and synthesis of heterocyclic malonyl–CoA decarboxylase inhibitors. Bioorganic & Medicinal Chemistry Letters, 16, 695–700. doi: 10.1016/j.bmcl.2005.10.020

Ohta, M., Suzuki, T., Koide, T. et al. (1996). Novel 5–hydroxytryptamine (5–HT3) receptor antagonists. I. Synthesis and structure–activity relationships of conformationally restricted fused imidazole derivatives. Chemical and Pharmaceutical Bulletin, 44 (5), 991–999. doi: 10.1248/cpb.44.991

Wolf, U. (1981). 7H–Imidazo[1.2–a]– und –[1.5–a]azepin–7–one. Zeitschrift fur Naturforschung B: Chemical Sciences, 36 (3), 383 – 385. doi: 10.1515/znb–1981–0321

Pizzirani, D., Roberti, M., Grimaudo, S. et al. (2009). Identification of biphenyl–based hybrid molecules able to decrease the intracellular level of bcl–2protein in bcl–2 overexpressing leukemia cells. Journal of Medicinal Chemistry, 52 (21), 6936–6940. doi: 10.1021/jm900907s

Dombrovskyy, V.A., Hracheva, E.V., Prokof’ev, E.P. (1989). Khimiko–Farmatsevticheskii Zhurnal, 23 (12), 1496–1498.

Leclaire, J., Mazari, M., Zhang, Y. et al. (2013). Bare histidine–serine models: implication and impact of hydrogen bondingon nucleophilicity. Chemistry A European Journal, 19 (34), 11301–11309. doi: 10.1002/chem.201301275

Karjalainen, A. J., Kurkela, K. O. A. (1987). Pat. USRE32400 E. Substituted imidazole derivatives and their use as anti–thrombosis agents. declared 30.07.1985; published 14.04.1987.

Hack, S., Wörlein, B., Höfner, G. et al. (2011). Development of imidazole alkanoic acids as mGAT3 selective GABA uptakeinhibitors. European Journal of Medicinal Chemistry, 46 (5), 1483–1498. doi: 10.1016/j.ejmech.2011.01.042

Amino, Y., Eto, H., Eguchi, C. (1989). Synthesis of 1,5–disubstituted imidazoles including an imidazole analogue of prostaglandin from 4(5)–hydroxymethylimidazole. Chemical and Pharmaceutical Bulletin, 37 (6), 1481–1487. doi: 10.1248/cpb.37.1481

Deredas, D., Skowron, M., Salomon, E. et al. (2007). Stereocontrolled synthesis of enantiomeric imidazolopiperidinosesand imidazoloazepanoses using Wittig/dihydroxylation reactions. Tetrahedron, 63 (13), 2915–2922. doi: 10.1016/j.tet.2007.01.016

Lawson, J. K. (1953). 2–Vinylimidazole and 1–methyl–2–vinylimidazole. Journal of the American Chemical Society, 75 (14), 3398–3400. doi: 10.1021/ja01110a029

Karjalainen, A. J., Pelkonen, R. O. (1995). Pat. US5439928 A. Aromatase inhibiting 4(5)–imidazoles. declared 19.05.1993; published 08.08.1995.

Sartori, G., Lancini, G. C., Cavalleri B. (1978). Synthesis of 5–substituted 1–methyl–2–nitro–1H–imidazoles (2–l4C. Journal of Labelled Compounds and Radiopharmaceuticals, 15 (S1), 673–680. doi: 10.1002/jlcr.2580150180

Pat. EP2095819 A1 (2008). N–Benzyl imidazole derivatives and their use as aldosterone synthase inhibitors. declared 28.02.2008; published 02.09.2009.

Rendy, R., Zhang, Y., McElrea, A. et al. (2008). Superacid–catalyzed reactions of cinnamic acids and the role ofsuperelectrophiles. The Journal of Organic Chemistry, 69 (7), 2340–2347. doi: 10.1021/jo030327t

Clark, B. A. J., Despinoy, X. L. M., McNab, H. et al. (1999). Pyrolytic cyclisation reactions of 3–azolylpropenyl alcohols; unexpectedly facile thermal decomposition of 5H–pyrrolo–[2,1–a]isoindole. Journal of the Chemical Society, Perkin Transactions 1, 15, 2049–2051. doi: 10.1039/A904884G

Pollak, A., Polanc, S., Stanovnik, B. et al. (1972). Uber ringoffnungen einiger azolo– und azinoazine. Monatshefte fur Chemie, 103 (6), 1591–1603. doi: 10.1007/BF00904613

Pollak, A., Stanovnik, B., Tišler, M. (1971). Pyridazines. XLVI. Ring opening of some azolo andazino pyridazines. Synthetic Communications, 1 (4), 289–293. doi: 10.1080/00397917108082711

Rothenberg, V. A. S., Dauplaise, D. L., Punier, H. P. (1983). Ein einfacher weg zu 2–vinylimidazolen. Angewandte Chemie, 95 (7), 573–574. doi: 10.1002/ange.19830950727

Arshad, N., Hashim, J., Kappe, C. O. (2009). Palladium(0)–catalyzed, copper(I)–mediated coupling of cyclic thioamides with alkenylboronic acids, organostannanes, and siloxanes. The Journal of Organic Chemistry, 74 (14), 5118–5121. doi: 10.1021/jo900848s

Rothenberg, A. S., Panzer, H. P., Schmitt, J. L. et al. (1983). Pat. US4410706. Preparation of Z–vinylimidazoles by dehydrogenation of Z–ethylimidazoles and Z–ethylimidazolines. declared 19.05.1982; published 18.10.1983.

Chen, Y., Dias, H. V. R., Lovely, C.J. (2003). Synthesis of fused bicyclic imidazoles by ring–closing metathesis. Tetrahedron Letters, 44 (7), 1379–1382. doi:10.1016/S0040–4039(02)02864–2

Benhida, R., Lezama, R., Fourrey, J.–L. (1998). First total Synthesis of fungerin an antifungal alkaloid from Fusarium sp. Tetrahedron Letteres, 39 (33), 5963–5964. doi: 10.1016/S0040–4039(98)01203–9

Haapalinna, A., Huhtala, P., Karjalainen, A. (2004). Pat. EP1261588 B1. Imidazole compounds as alpha 2–adrenoceptors antagonists. declared 12.01.2001; published 20.10.2004.

Karjalainen, A., Huhtala, P., Savola, J.–M. (2001). Pat. US6313311 B1. Imidazole derivatives having affinity for alpha2 receptors. declared 02.10.1996; published 06.11.2001.

Lovely, C. J,. Du, H., Sivappa R. (2007). Preparation and Diels–Alder chemistry of 4–vinylimidazoles. The Journal of Organic Chemistry, 72 (10), 3741–3749. doi: 10.1021/jo0626008

Gorugantula, S. P., Carrero–Martınez, G. M., Dantale, S. W. et al. (2010). Palladium–catalyzed reductive N–heterocyclization of alkenyl–substituted nitroarenes as a viable method for the preparation of bicyclic pyrrolo–fused heteroaromatic compounds. Tetrahedron, 66 (10), 1800–1805. doi: 10.1016/j.tet.2010.01.029

Li, A., Gilbert, T. M., Klumpp, D. A. (2008). Preparation of aza–polycyclic aromaticcompounds via superelectrophilic cyclizations. The Journal of Organic Chemistry, 73 (9), 3654–3657. doi: 10.1021/jo8003474

Chornous, V. A., Melnik, O. Ya., Melnik, D. A. et al. (2015). Polyfunctional imidazoles: XI. Reaction of 1–aryl–4–chloro–5–(2–nitrovinyl)–1H–imidazoles with nonstabilized azomethine ylides. Synthesis of (1–aryl–4–chloro–1H–imidazol–5–yl)–substituted nitropyrrolidines and nitropyrrolizines. Russian Journal Organic Chemistry, 51 (10), 1423–1429. doi: 10.1134/S1070428015100115

Chornous, V. O., Melnik, O. Ya., Melnik, D. O. et al. (2016). Ukrainskii Khimicheskii Zhurnal, 82 (5), 44–52.

Melnik, O. Ya., Chornous, V. A., Vovk, M. V. (2015). Polyfunctional imidazoles: IX. Synthesis of 1–aryl–5–(2–aryl–3,4–dihydro–2H–pyrrol–4–yl)–4–chloro–1H–imidazoles. Russian Journal Organic Chemistry, 51 (2), 240–244. doi: 10.1134/S1070428015020189

Baker, D. C., Putt, S. R., Showalter, H. D. H. (1983). Studies related to the total synthesis of pentostatin. Approaches to the synthesis of (8R)–3,6,7,8–tetrahydroimidazo–[4,5–d][l,3]diazepin–8–ol and N–3 alkyl congeners. Journal of Heterocyclic Chemistry, 20 (3), 629–634. doi: 10.1002/jhet.5570200324

Baker, D.C., Putt, S.R. (1979). A total synthesis of pentostatin, the potent inhibitor of adenosine deaminase. Journal of American Chemical Society, 101(20), 6127–6128. doi: 10.1021/ja00514a048

Keller, M., Trankle, C., She, X. et al. (2015). M2 Subtype preferring dibenzodiazepinone–type muscarinic receptor ligands: Effect of chemical homo–dimerization on orthosteric (and allosteric) binding. Bioorganic & Medicinal Chemistry, 23 (14), 3970–3990. doi: 10.1016/j.bmc.2015.01.015

Aulaskari, P., Ahlgren, M., Vainiotalo, P. (2000). Preparation of 1–substituted–5–[(2–oxo–2–phenyl)ethyl]imidazoles. Journal of Heterocyclic Chemistry, 37 (1), 87–93. doi: 10.1002/jhet.5570370114

Aulaskari, P., Pohjalab, E., Vainiotalo, P. (1997). Synthesis of 1–substituted–5–[(2–nitro–2–phenyl)–ethyl]imidazoles. Synthetic Communications, 27 (15), 2627–2635. doi: 10.1080/00397919708004132

Le, P. Q., Nguyen, T. S., May, J. A. (2012). A general method for the enantioselective synthesis of α‑chiral heterocycles. Organic Letters, 14 (23), 6104–6107. doi: 10.1021/ol3030605

Guerin, D. J., Miller, S. J. (2002). Asymmetric azidation–cycloaddition with open–chain peptide–based catalysts. A sequential enantioselective route to triazoles. Journal of American Chemical Society, 124 (10), 2134–2136. doi: 10.1021/ja0177814


GOST Style Citations


1.         Fromtling, R. A. Overview of medically important antifungal azole derivatives / R. A. Fromtling // Clin. Microbiol. Rev. – 1988. – Vol. 1, Issue 2. – P. 187–217. doi: 10.1128/CMR.1.2.187

2.         Preparation and antiarthritic and analgesic activity of 4,5–diaryl–2–(substituted thio)–1H–imidazoles and their sulfoxides and sulfones / T. R. Sharpe, S. C. Cherkofsky, W. E. Hewes et al. // J. Med. Chem. – 1985. – Vol. 28, Issue 9. – P. 1188–1194. doi: 10.1021/jm00147a011

3.         Ucucu, U. Synthesis and analgesic activity of some 1–benzyl–2–substituted–4,5–diphenyl–1H–imidazole derivatives / U. Ucucu, N. G. Karaburun,I.Isikdag // Il Farmaco. – 2001. – Vol. 56, Issue 4. – P. 285–290. doi: 10.1016/S0014–827X(01)01076–X

4.         The neuroprotective action of JNK3 inhibitors based on the 6,7–dihydro–5H–pyrrolo[1,2–a]imidazole scaffold / P. P. Graczyk, A. Khan, G. S. Bhatia et al. // Bioorg. Med. Chem. Lett. – 2005. – Vol. 15, Issue 21. – P. 4666–4670. doi: 10.1016/j.bmcl.2005.07.076

5.         Laufer, S. A. Tetrasubstituted imidazole inhibitors of cytokine release : probing substituents in the N–1 position / S. A. Laufer, W. Zimmermann, K. J. Ruff // J. Med. Chem. – 2004. – Vol. 47, Issue 25. – P. 6311–6325. doi: 10.1021/jm0496584

6.         Black, J. W. Sulphur–methylene isosterism in the developent of metiamide, a new histamine H2–receptor antagonist / J. W. Black, G. J. Durant, J. C. Emmett // Nature. – 1974. – Vol. 248, Issue 5443. – P. 65–67. doi: 10.1038/248065a0

7.         Jin, Z. Muscarine, imidazole, oxazole and thiazole alkaloids / Z. Jin // Nat. Prod. Rep. – 2009. – Vol. 26, Issue 3. – P. 382–445. doi: 10.1039/B718045B

8.         Jin, Z. Imidazole, oxazole and thiazole alkaloids / Z. Jin // Nat. Prod. Rep. – 2006. – Vol. 23, Issue 3. – P. 464–498. doi: 10.1039/B502166A

9.         Jin, Z. Muscarine, imidazole, oxazole and thiazole alkaloids / Z. Jin // Nat. Prod. Rep. – 2005. – Vol. 22, Issue 2. – P. 196–229. doi: 10.1039/B316104H

10.       Imidazole alkaloids from lepidium meyenii / B. Cui, B. L. Zheng, K. He et al. // J. Nat. Prod. – 2003. – Vol. 66, Issue 8. – P. 1101–1103. doi: 10.1021/np030031i

11.       Grimmett, M. R. Imidazole and benzimidazole synthesis / M. R. Grimmett. –London: Academic Press, 1997. – 265 p.

12.       Katritzki, A. R. Comprehensive heterocyclic chemistry / A. R. Katritzki, C. W. Rees. – Elsevier Sci. Ltd, 1997. –Vol. 5. – 994 p.

13.       Substituted imidazoles and 2–imidazolines / L. P. Kyrides, F. R. Zienty, G. W. Steahly et al. // J. Org. Chem. – 1947. – Vol. 12, Issue 4. – P. 557–586. doi: 10.1021/jo01168a015

14.       Synthesis of L–histidine specifically labelled with stable isotopes / J. J. Cappon, K. D. Witters, J. Baart et al. // Recl. Trav. Chim. Pays–Bas. – 1994. – Vol. 113, Issue 6. – P. 318–328. doi: 10.1002/recl.19941130603

15.       Peptide mimetics of thyrotropin–releasing hormone based on a cyclohexaneframework design, synthesis, and cognition–enhancing properties / G. L. Olson, H.–C. Cheung, E. Chiang et al. // J. Med. Chem. – 1995. – Vol. 38, Issue 15. – P. 2866–2879. doi: 10.1021/jm00015a009

16.       Pat. US4812473 A (1989). 1,5–Disubstituted imidazoles as inhibitors of juvenile hormone / Kuwano E., Takeya R., Eto M.; Earth Chemical Co., Ltd. – declared 24.03.1987 ; published 14.03.1989.

17.       Fluorinated analogues of the imidazole insect growth regulator KK–42 / C. Arbonés, F. J. Sánchez, M.–P. Marco et al. // Heterocycles. – 1990. – Vol. 31, Issue 1. – P. 67–78. doi: 10.3987/COM–89–5125

18.       Shafiee, A. Syntheses of 2–(2–arylethyl)imidazoles / A. Shafiee, N. Rastkary, A. Foroumadi // J. Heterocycl. Chem. – 1998. – Vol. 35, Issue 3. – P. 607–610. doi: 10.1002/jhet.5570350319

19.       Chemotherapeutic nitroheterocycles. Antischistosomal properties of nitrofurylvinyl and nitrothienylvinyl heterocycles / D. W. Henry, V. H. Brown, M. Cory et al. // J. Med. Chem. – 1973. – Vol. 16, Issue 11. – P. 1287–1291. doi: 10.1021/jm00269a015

20.       Pat. US3993643 A (1976). N–substituted 2–[2–(5–nitro–2–furyl)vinyl]imidazoles / Henry D. W., Cory M.; Stanford Research Institute. – declared 07.05.1976; published 23.11.1976.

21.       Evaluation of the side arm of (naphthylvinyl)pyridinium inhibitors of choline acetyltransferase / J. F. DeBernardis, P. Gifford, M. Rizk et al. // J. Med. Chem. – 1988. – Vol. 31, Issue 1. – P. 117–121. doi: 10.1021/jm00396a017

22.       Suwiriski, J. Nitroimidazoles XVII. Nucleophilic amination or ring transformation in reactions of l–aryl–4–nitroimidazoles with 4–amino–1,2,4–triazole or hydroxylamine / J. Suwiriski, K. Swierczek // Tetrahedron. – 1993. – Vol. 49, Issue 24. – P. 5339–5350. doi: 10.1016/S0040–4020(01)82383–8

23.       Allsebrook, W. E. The constitution of purine nucleosides. Part X. A new synthesis of xanthine and attempted syntheses of xanthine glucosides from glyoxalines / W. E. Allsebrook, J. M. Gulland, L. F. Story // J. Chem. Soc. – 1942. – P. 232–236. doi: 10.1039/JR9420000232

24.       Baddiley, J. Chemical studies in the biosynthesis of purine nucleotides. Part 111. The synthesis of 5–amino–l–(β–D–ribofuranosyl)glyoxaline–4–carboxyamide and 4–amino–l–(β–D–ribofuranosyl)glyoxaline–5–carboxyamide // J. Baddiley, J. G. Buchanan, F. E. Hardy // J. Chem. Soc. – 1959. – P. 2893–2901. doi: 10.1039/JR9590002893

25.       Analogs of iso–azepinomycin as potential transition–state analog inhibitors ofguanase : synthesis, biochemical screening, and structure–activity correlations ofvarious selectively substituted imidazo[4,5–e][1,4]diazepines / S. Tantravedi,S. Chakraborty, N. H. Shah et al. // Bioorg. Med. Chem. – 2013. – Vol. 21, Issue 17. – P. 4893–4903. doi: 10.1016/j.bmc.2013.06.069

26.       Giraldi, P. N. Antiprotozoans. Synthesis and biological activity of some styrylimidazole derivatives / P. N. Giraldi, V. Mariotti,I.De Carneri // J. Med. Chem. – 1968. – Vol. 11, Issue 1. – P. 66–70. doi: 10.1021/jm00307a014

27.       Total synthesis of (8R)–3–(2–deoxy–β–D–erythro–pentofuranosyl)–3,6,7,8–tetrahydroimidazo[4,5–d][1,3]diazepin–8–ol (pentostatin), the potent inhibitor of adenosine deaminase / E. Chan, S. R. Putt, H. D. H. Showalter et al. // J. Org. Chem. – 1982. – Vol. 47, Issue 18. – P. 3457–3464. doi: 10.1021/jo00139a015

28.       Asato, G. Nitroheterocyclic antimicrobial agents. 1–Methyl–2–nitro–5–imidazolyl derivatives / G. Asato, G. Berkelhammer // J. Med. Chem. – 1972. – Vol. 15, Issue 10. – P. 1086–1088. doi: 10.1021/jm00280a030

29.       Cavalleri, B. Synthesis of 1–alkyl–2–nitroimidazole–5–carboxaldehydes / B. Cavalleri, R. Ballotta, G. C. Lancini // J. Heterocycl. Chem. – 1972. – Vol. 9, Issue 5. – P. 979–984. doi: 10.1002/jhet.5570090502

30.       New 5–substituted 1–alkyl–2–nitroimidazoles / B. Cavalleri, R. Ballotta, V. Arioli et al. // J. Med. Chem. – 1973. – Vol. 16, Issue 5. – P. 557–560. doi: 10.1021/jm00263a035

31.       Cavalleri, B. Synthesis and biological activity of some vinyl–substituted 2–nitroimidazoles / B. Cavalleri, G. Volpe, V. Arioli // J. Med. Chem. – 1977. – Vol. 20, Issue 5. – P. 656–660. doi: 10.1021/jm00215a007

32.       Burnett, F. N. Synthesis of a novel ring–expanded purine analogue containing a5:8–fused imidazo[4,5–e][1,2,4]triazocine ring system amidstopportunistic rearrangements and ring transformations / F. N. Burnett, R. S. Hosmane // Tetrahedron. – 2002. – Vol. 58, Issue 47. – P. 9567–9578. doi: 10.1016/S0040–4020(02)01252–8

33.       Hosmane, R. S. Facile conversion of 4(5)–nitro–5(4)–methylimidazoles into4(5)–nitro–5(4)–cyanoimidazoles / R. S. Hosmane, A. Bhan, M. E. Rauser // J. Org. Chem. – 1985. – Vol. 50, Issue 26. – P. 5892–5895. doi: 10.1021/jo9824910

34.       Burnett, F. N. Imidazo[4,5–e][1,2,4]triazocine : a novel 5 : 8–fused ring system riddled with rearrangements / F. N. Burnett, R. S. Hosmane // Heterocycl. Commun. – 1997. – Vol. 45, Issue 5. – P. 857–861. doi: 10.3987/COM–97–7783

35.       Ross, W. J. Antiparasitic nitroimidazoles. 7. Some 4– and 5–styrylnitroimidazoles / W. J. Ross, A. Todd // J. Med. Chem. – 1973. – Vol. 16, Issue 7. – P. 863–865. doi: 10.1021/jm00265a030

36.       Burnett, F. N. Synthetic approaches to 5:8–fused heterocyclic systems. A novel rearrangement during the synthesis of imidazo[4,5–e][1,2,4]triazocine ring system / F. N. Burnett, R. S. Hosmane // Nucleosides & Nucleotides. – 1995. – Vol. 14, Issue 3–5. – P. 325–328. doi: 10.1080/15257779508012373

37.       Siddiqui, S. Synthetic analogue of stilbene containing an imidazole nucleus / S. Siddiqui, R. S. Hosmane // Molecules. – 2000. – Vol. 5, Issue 6. – P. 856–863. doi: 10.3390/50600856

38.       Aza–analogs of stilbene with a dipolar character. (E)–1–alkyl–(2–(azolyl–2–idene)etylidene)–dihydropyridines and (E)–2–(2–(1–alkyl–3–pyridinium)vinyl)azolate inner salts / E. Alcalde, T. Roca, J. P. Fayet et al. // Chem. Lett. – 1991. – Vol. 20, Issue 12. – P. 2151–2154. doi: 10.1246/cl.1991.2151

39.       Alcalde, E. Heterocyclic betaines. 14. (E)–l–Alkyl–[2–(imidazol–2–ylidene)ethylidene]dihydropyridines with a betaine character. An improved protocol for a Knoevenagel–type condensation for synthesis of(E)–l–alkyl–[2–(1H–imidazol–2–yl)vinyl]pyridinium salts / E. Alcalde, T. Roca // J. Org. Chem. – 1992. – Vol. 57, Issue 18. – P. 4834–4838. doi: 10.1021/jo00044a015

40.       Studies on the interactions of the new 2,6–bis[2–(heteroaryl)vinyl]–1–methylpyridinium cations with the decamer d(CGTACGTACG)2 / M. Fichera, C. G. Fortuna, G. Impallomeni et al. // Eur. J. Org. Chem. – 2002. – Vol. 2002, Issue 1. – P. 145–150. doi: 10.1002/1099–0690(20021)2002

41.       An improved synthesis of 3–methyl–4–nitro–5–heteroarylethenylisoxazoles / M. F. A. Adamo, E. F. Duffy, V. R. Konda et al. // Heterocycles. – 2007. – Vol. 71, Issue 5. – P. 1173–1181. doi: 10.3987/COM–07–11023

42.      Pat. US5098923 A (1992). Aromatase inhibiting 4(5)–imidazoles / Karjalainen A. J., Kangas L. V. M., Kurkela K. O. A.; Farmos–Yhtyma Oy. – declared 27.09.1990 ; published 24.03.1992.

43.       McNab, H. New synthetic routes to pyrrolo–[1,2–a]– and –[1,2–c]–imidazol–5–ones by flash vacuum pyrolysis / H. McNab, C. Thornley // J. Chem. Soc. Perkin Trans. 1. – 1997. – Issue 15. – P. 2203–2209. doi: 10.1039/A701751K

44.       Synthesis of a new imidazo[4,5–b]pyridin–5–one via a vicarious nucleophilic substitution of hydrogen / M. D. Crozet, C. Suspеne, M. Kaafarani et al. // Heterocycl. Commun. – 2004. – Vol. 63, Issue 7. – P. 1629–1635. doi: 10.3987/COM–04–10069

45.       Potent nonpeptfde angiotensin II receptor antagoqists. 2. 1–(Carboxybenzyl)imidazole–5–acrylic acids / R. M. Keenan, J. Weinstock, J. A. Finkelstein et al. // J. Med. Chem. – 1993. – Vol. 36, Issue 13. – P. 1880–1892. doi: 10.1021/jm00065a011

46.       Synthesis of new potent and selective aromatase inhibitors based on long–chained diarylalkylimidazole and diarylalkyltriazole molecule skeletons / A. Karjalainen, A. Kalapudas, M. Sodervall et al. // Eur. J. Pharm. Sci. – 2000. – Vol. 11, Issue 7. – P. 109–131. doi: 10.1016/S0928–0987(00)00074–9

47.       Structure–activity relationship of chalcones and related derivatives as ligands for detecting of β–amyloid plaques in the brain / M. Ono, M. Hori, M. Haratake et al. // Bioorg. Med. Chem. – 2007. – Vol. 15, Issue 19. – P. 6388–6396. doi: 10.1016/j.bmc.2007.06.055

48.       Pat. EP2030635 A1 (2009). Composition for diagnosing amyloid–related disease / Nakayama M., Haratake M., Ono M.;NagasakiUniversity. – declared 22.05.2007; published 04.03.2009.

49.       Pat. US6071943 A (2000). Іmidazole derivative and medicinecomprising the same as activeingredient / Shioiri N., Mikami T., Morimoto S. et al.; SSP Co. Ltd. – declared 30.11.98 ; published 06.06.00.

50.       Identification of a novel class of covalent modifiersof hemoglobin as potential antisickling agents / A. M. Omar, M. A. Mahran, M. S. Ghatge et al. // Org. Biomol. Chem. – 2015. – Vol. 13, Issue 22. – P. 6353–6370. doi: 10.1039/c5ob00367a

51.       Synthesis, SAR and antibacterial studies on novel chalcone oxazolidinone hybrids / N. Selvakumar, G. S. Kumar, A. M. Azhagan et al. // Eur. J. Med. Chem. – 2007. – Vol. 42, Issue 4. – P. 538–543. doi: 10.1016/j.ejmech.2006.10.013

52.       Синтез та антимікробна активність 4–хлоро–5–(2–нітровініл)–1–Н–імідазолів і продуктів їх взаємодії з 3–метил–2–піразолін–5–оном / В. О. Чорноус, О. Я. Мельник, А. М. Грозав та ін. // ЖОФХ. – 2014. – Т. 12, № 3 (47). – С. 28–32.

53.       Polyfunctional imidazoles : X. Synthesis of 4–chloro–5–(2–nitroalkenyl)–1H–imidazoles and their reaction with 5–methyl–2,4–dihydro–3H–pyrazol–3–one / V. A. Chornous, A. N. Grozav, O. Ya. Mel’nik et al. // Russ. J. Org. Chem. – 2015. – Vol. 51, Issue 4. – С. 251–257. doi: 10.1134/S1070428015040132

54.       Синтез і антимікробна активність нових 3–(імідазол–5–іл)–1–арил–2–пропен–1–онів і отриманих на їх основі 1Н–піразолінів / В. О. Чорноус, О. Я. Мельник, Р. В. Куцик та ін. // Наук. вісник Чернівецького університету. – Зб. наук. праць. – Вип. 683. – «Хімія». – Чернівці : Чернівецький національний університет. – 2014. – С. 90–96.

55.       Синтез, гіпоглікемічна активність та гостра токсичність нових імідазол–тіазолідинових гібридних структур / В. О. Чорноус, О. Я. Мельник, О. М. Глебов та ін. // ЖОФХ. – 2016. – Т. 14, № 1 (53). – С. 46–52.

56.       Синтез (1–арил–4–хлоро–1Н–імідазол–5–іл)оцтових кислот / О. Мельник, Д. Мельник, В. Чорноус та ін. // Вісник Львівського університету. Серія хімічна. – 2016. – Вип. 57, Ч. 2. – С. 280–285.

57.       Kokosa, J. M. Practical multigram synthesis for 4(5)–vinylimidazole / J. M. Kokosa, R. A. Szafasz, E. Tagupa // J. Org. Chem. – 1983. – Vol. 43, Issue 20. – P. 3605–3607. doi: 10.1021/jo00168a062

58.       Design and synthesis of heterocyclic malonyl–CoA decarboxylase inhibitors / J.–F. Cheng, M. Chen, B. Liu et al. // Bioorg. Med. Chem. Lett. – 2006. – Vol. 16. – P. 695–700. doi: 10.1016/j.bmcl.2005.10.020

59.       Novel 5–hydroxytryptamine (5–HT3) receptor antagonists. I. Synthesis and structure–activity relationships of conformationally restricted fused imidazole derivatives / M. Ohta, T. Suzuki, T. Koide et al. // Chem. Pharm. Bull. – 1996. – Vol. 44, Issue 5. – P. 991–999. doi: 10.1248/cpb.44.991

60.       Wolf, U. 7H–Imidazo[1.2–a]– und –[1.5–a]azepin–7–one / U. Wolf // Z. Naturforsch., B : Chem. Sci. – 1981. – Vol. 36, Issue 3. – P. 383 – 385. doi: 10.1515/znb–1981–0321

61.       Identification of biphenyl–based hybrid molecules able to decrease the intracellular level of bcl–2protein in bcl–2 overexpressing leukemia cells / D. Pizzirani, M. Roberti, S. Grimaudo et al. // J. Med. Chem. – 2009. – Vol. 52, Issue 21. – P. 6936–6940. doi: 10.1021/jm900907s

62.       Домбровский, В. А. Синтез гетероциклического аналога на основе имидазола / В. А. Домбровский, Е. В. Грачева, Е. П. Прокофьев // Хим.-фарм. журн. – 1989. – Т. 23, №. 12. – С. 1496–1498.

63.       Bare histidine–serine models : implication and impact of hydrogen bondingon nucleophilicity / J. Leclaire, M. Mazari,Y. Zhang et al. // Chem. Eur. J. – 2013. – Vol. 19, Issue 34. –P. 11301–11309. doi: 10.1002/chem.201301275

64.       Pat. USRE32400 E (1987). Substituted imidazole derivatives and their use as anti–thrombosis agents / Karjalainen A. J., Kurkela K. O. A.; Farmos Yhtyma Oy. – declared 30.07.1985 ; published 14.04.1987.

65.       Development of imidazole alkanoic acids as mGAT3 selective GABA uptakeinhibitors / S. Hack, B. Wörlein, G. Höfner et al. // Eur. J. Med. Chem. – 2011. – Vol. 46, Issue 5. – P. 1483–1498. doi: 10.1016/j.ejmech.2011.01.042

66.       Amino, Y. Synthesis of 1,5–disubstituted imidazoles including an imidazole analogue of prostaglandin from 4(5)–hydroxymethylimidazole / Y. Amino, H. Eto, C. Eguchi // Chem. Pharm. Bull. – 1989. – Vol. 37, Issue 6. – P. 1481–1487. doi: 10.1248/cpb.37.1481

67.       Stereocontrolled synthesis of enantiomeric imidazolopiperidinosesand imidazoloazepanoses using Wittig/dihydroxylation reactions / D. Deredas, M. Skowron, E. Salomon et al. // Tetrahedron. – 2007. – Vol. 63, Issue 13. – P. 2915–2922. doi: 10.1016/j.tet.2007.01.016

68.       Lawson, J. K. 2–Vinylimidazole and 1–methyl–2–vinylimidazole / J. K. Lawson // J. Am. Chem. Soc. – 1953. – Vol. 75, Issue 14. – P. 3398 – 3400. doi: 10.1021/ja01110a029

69.       Pat. US5439928 A (1995). Aromatase inhibiting 4(5)–imidazoles / Karjalainen A. J.. Pelkonen R. O.; M.–L. Sodervall; Orion–Yhtyma Oy. – declared 19.05.1993 ; published 08.08.1995.

70.       Sartori, G. Synthesis of 5–substituted 1–methyl–2–nitro–1H–imidazoles (2–l4C) / G. Sartori, G. C. Lancini, B. Cavalleri // J. Labell. Compd. Radiopharm. – 1978. – Vol. 15, Issue S1. – P. 673–680. doi: 10.1002/jlcr.2580150180

71.       Pat. EP2095819 A1 (2008). N–Benzyl imidazole derivatives and their use as aldosterone synthase inhibitors / The designation of the inventor has not yet been filed;MaastrichtUniversity. – declared 28.02.2008 ; published 02.09.2009.

72.       Superacid–catalyzed reactions of cinnamic acids and the role ofsuperelectrophiles / R. Rendy, Y. Zhang, A. McElrea et al. // J. Org. Chem. – 2004. – Vol. 69, Issue 7. – P. 2340–2347. doi: 10.1021/jo030327t

73.       Pyrolytic cyclisation reactions of 3–azolylpropenyl alcohols; unexpectedly facile thermal decomposition of 5H–pyrrolo–[2,1–a]isoindole / B. A. J. Clark, X. L. M. Despinoy, H. McNab et al. // J. Chem. Soc., Perkin Trans. 1. – 1999. – Issue 15. – P. 2049–2051. doi: 10.1039/A904884G

74.       Über Ringöffnungen einiger Azolo– und Azinoazine / A. Pollak, S. Polanc, B. Stanovnik et al. // Monatshch. Chem. – 1972. – Vol. 103, Issue 6. – P. 1591–1603. doi: 10.1007/BF00904613

75.       Pollak, A. Pyridazines. XLVI. Ring opening of some azolo andazino pyridazines / A. Pollak, B. Stanovnik, M. Tišler // Synth. Commun. – 1971. – Vol. 1, Issue 4. – P. 289–293. doi: 10.1080/00397917108082711

76.      Rothenberg, V. A. S. Ein einfacher Weg zu 2–vinylimidazolen / V. A. S. Rothenberg, D. L. Dauplaise, H. P. Punier // Angew. Chem. – 1983. – Vol. 95, Issue 7. – P. 573–574. doi: 10.1002/ange.19830950727

77.       Arshad, N. Palladium(0)–catalyzed, copper(I)–mediated coupling of cyclic thioamides with alkenylboronic acids, organostannanes, and siloxanes / N. Arshad, J. Hashim, C. O. Kappe // J. Org. Chem. – 2009. – Vol. 74, Issue 14. – P. 5118–5121. doi: 10.1021/jo900848s

78.       Pat. US4410706 (1983). Preparation of Z–vinylimidazoles by dehydrogenation of Z–ethylimidazoles and Z–ethylimidazolines / Rothenberg A. S., Panzer H. P., Schmitt J. L. et al.; American Cyanamid Company. declared 19.05.1982 ; published 18.10.1983.

79.       Chen, Y. Synthesis of fused bicyclic imidazoles by ring–closing metathesis / Y. Chen, H. V. R. Dias, C. J. Lovely // Tetrahedron Lett. – 2003. – Vol. 44, Issue 7. – P. 1379–1382. doi:10.1016/S0040–4039(02)02864–2

80.       Benhida, R. First total Synthesis of fungerin an antifungal alkaloid from Fusarium sp. / R. Benhida, R. Lezama, J.–L. Fourrey // Tetrahedron Lett. – 1998. – Vol. 39, Issue 33. – P. 5963–5964. doi: 10.1016/S0040–4039(98)01203–9

81.       Pat. EP1261588 B1 (2004). Imidazole compounds as alpha 2–adrenoceptors antagonists / Haapalinna A., Huhtala P., Karjalainen A.; Orion Corporation. – declared 12.01.2001 ; published 20.10.2004.

82.       Pat. US6313311 B1 (2001). Imidazole derivatives having affinity for alpha2 receptors / Karjalainen A., Huhtala P., Savola J.–M.; Orion Corporation. – declared 02.10.1996 ; published 06.11.2001.

83.       Preparation and Diels–Alder chemistry of 4–vinylimidazoles / C. J. Lovely, H. Du, R. Sivappa et al. // J. Org. Chem. – 2007. – Vol. 72, Issue 10. – P. 3741–3749. doi: 10.1021/jo0626008

84.       Palladium–catalyzed reductive N–heterocyclization of alkenyl–substituted nitroarenes as a viable method for the preparation of bicyclic pyrrolo–fused heteroaromatic compounds / S. P. Gorugantula, G. M. Carrero–Martınez, S. W. Dantale et al. // Tetrahedron. – 2010. – Vol. 66, Issue 10. – P. 1800–1805. doi: 10.1016/j.tet.2010.01.029

85.       Li, A. Preparation of aza–polycyclic aromaticcompounds via superelectrophilic cyclizations / A. Li, T. M. Gilbert, D. A. Klumpp // J. Org. Chem. – 2008. – Vol. 73, Issue 9. – P. 3654–3657. doi: 10.1021/jo8003474

86.       Polyfunctional imidazoles : XI. Reaction of 1–aryl–4–chloro–5–(2–nitrovinyl)–1H–imidazoles with nonstabilized azomethine ylides. Synthesis of (1–aryl–4–chloro–1H–imidazol–5–yl)–substituted nitropyrrolidines and nitropyrrolizines / Chornous V. A., Mel’nik O. Ya., Mel’nik D. A. et al. // Russ. J. Org. Chem. – 2015. – Vol. 51, Issue 10. – P. 1454–1460. doi: 10.1134/S1070428015100115

87.       2–(5–Імідазоліл)заміщені 3–нітрохромени: синтез, квантово–хімічне дослідження та піролідино– і триазолоанелювання / В. О. Чорноус, О. Я. Мельник, Д. О. Мельник, М. В. Вовк // Укр. хім. журн. – 2016. – Т. 82, № 5. – С. 44–52.

88.       Mel’nik, O.Ya. Polyfunctional imidazoles: IX. Synthesis of 1–aryl–5–(2–aryl–3,4–dihydro–2H–pyrrol–4–yl)–4–chloro–1H–imidazoles / V. A. Chornous, O. Ya. Mel’nik, M. V. Vovk // Russ. J. Org. Chem. – 2015. – Vol. 51, Issue 2. – P. 240–244. doi: 10.1134/S1070428015020189

89.       Baker, D. C. Studies related to the total synthesis of pentostatin. Approaches to the synthesis of (8R)–3,6,7,8–tetrahydroimidazo–[4,5–d][l,3]diazepin–8–ol and N–3 alkyl congeners / D. C. Baker, S. R. Putt, H. D. H. Showalter // J. Heterocyclic Chem. – 1983. – Vol. 20, Issue 3. – P. 629–634. doi: 10.1002/jhet.5570200324

90.       Baker, D. C. A total synthesis of pentostatin, the potent inhibitor of adenosine deaminase / D. C. Baker, S. R. Putt // J. Amer. Chem. Soc. – 1979. – Vol. 101, Issue 20. – P. 6127–6128. doi: 10.1021/ja00514a048

91.       M2 Subtype preferring dibenzodiazepinone–type muscarinic receptor ligands: Effect of chemical homo–dimerization on orthosteric (and allosteric) binding / M. Keller, C. Trankle, X. She et al. // Bioorg. Med. Chem.– 2015. – Vol. 23, Issue 14. – P. 3970–3990. doi: 10.1016/j.bmc.2015.01.015

92.       Aulaskari, P. Preparation of 1–substituted–5–[(2–oxo–2–phenyl)ethyl]imidazoles / P. Aulaskari, M. Ahlgren, P. Vainiotalo // J. Heterocycl. Chem. – 2000. – Vol. 37, Issue 1. – P. 87–93. doi: 10.1002/jhet.5570370114

93.       Aulaskari, P. Synthesis of 1–substituted–5–[(2–nitro–2–phenyl)–ethyl]imidazoles / P. Aulaskari,E. Pohjalab, P. Vainiotalo // Synth. Commun.– 1997. – Vol. 27, Issue 15. – P. 2627–2635. doi: 10.1080/00397919708004132

94.       Le, P. Q. A general method for the enantioselective synthesis of α‑chiral heterocycles / P. Q. Le, T. S. Nguyen, J. A. May // Org. Lett. – 2012. – Vol. 14, Issue 23. – P. 6104–6107. doi: 10.1021/ol3030605

95.       Guerin, D. J. Asymmetric azidation–cycloaddition with open–chain peptide–based catalysts. A sequential enantioselective route to triazoles / D. J. Guerin, S. J. Miller // J. Am. Chem. Soc. – 2002. – Vol. 124, Issue 10. – P. 2134–2136. doi: 10.1021/ja0177814





DOI: https://doi.org/10.24959/ophcj.17.920

Abbreviated key title: Ž. org. farm. hìm.

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