Esters of 4-formylpyrazol-3-carboxylic acids

Authors

  • M. K. Bratenko Bukovinian State Medical University, Ukraine
  • M. M. Barus Bukovinian State Medical University, Ukraine
  • M. V. Vovk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.17.925

Keywords:

esters of 4-formylpyrazol-3-carboxylic acids, methods of synthesis, chemical properties, structural functionalization, polyfunctional derivatives

Abstract

The scientific publications devoted to chemistry of the synthetically promising bifunctional derivatives of pyrazole – esters of 4-formylepyrazole-3-carbonic acids have been generalized and systematized. A special attention has been given to description of two main synthetic approaches: 1) processes of the conjugated formation of aldehyde and ester groups, on one hand, and the pyrazolic system, on the other; 2) synthetic strategies targeted on functionalization of the pyrazolic nucleus. It has been shown that the first approach is performed usually by the scheme [3+2] meaning in situ cyclojoining of the generated nitrilimines or esters of diazoacetic acid with formylacetylenes or their derivatives followed by cyclization with simultaneous formylation of hydrazones and semicarbazones of pyruvic acid by Wilsmaer-Haack reagent. The second approach deals with formylation of esters of pyrazole-3-carbonic acids according to Wilsmaer-Haack reaction. As seen from the analysis of chemical properties of esters of 4-formylpyrazole-3-carbonic acids, the aldehyde group is the most typical target of their chemical transformations. Such transformations are reactions with nitrogen-containing nucleophiles, alkenylation, oxidation, reduction and other multicomponent reactions that can be considered as usual approaches to structural functionalization of the pyrazolic nucleus. Cyclocondensations are also important in this context since these processes involve formyl, ester and other functional groups obtained from them. These substances appeared to be effective substrates for construction of some biologically active pyrazolo[4,3-d]pyrimidine and pyrazolo [3,4-d]pyridazynic systems.

Downloads

Download data is not yet available.

References

  1. Chandanshive, J. Z., Bonini, B. F., Gentili, D. et al. (2010). Regiocontrolled Synthesis of Ring–Fused Thieno[2,3–c]py–razoles through 1,3–Dipolar Cycloaddition of Nitrile Imines with Sulfur–Based Acetylenes. European Journal of Medicinall Chemistry, 2010 (33), 6440–6447. doi: 10.1002/ejoc.201001048
  2. Margorskaya, O. I., Medvedeva, A. S., Demina, M. M. et al. (1989). The aldol–type condensation of methyl diazoacetate with 3–organyl–silyl and –germyl propynals and their carbon analogues. Journal of Organometallic Chemistry, 376 (1), 31–40. doi: 10.1016/0022–328X(89)88071–4
  3. Medvedeva, A. S., Demina, M. M., Borisova, A. I. et al. (1981). Reacting 1–triethylgermil–1–propyn–3–al with methyl ester of diazoacetic acid. Tautomeric dimerization tiriethygermil–3–formyl–4–karbometoksipirazol. Journal of general chemistry of the U.S.S.R. in English translation, 51 (6), 1324–1328.
  4. Medvedeva, A. S., Demina, M. M., Protsuk, N. I. et al. (1980). Interaction of some diazоalkanes trialkylsilyl(germyl)propionales. Journal of general chemistry of the U.S.S.R. in English translation, 50 (6), 1775–1779.
  5. Henkel, K., Weygand, F. (1943). Synthese von Pyrazol – und Triazoldialdehyden. Chemische Berichte, 76 (8), 812–818. doi: 10.1002/cber.19430760809
  6. Devasthale, P., Washburn, W. N., Wang, W. et al. (2010). Azolopyrrolone melanin concentrating hormone receptor–1 antagonists. Pat. WO 2010/47956 A1. № PCT/US2009/059924; declared 08.08.2009; published 29.04.2010.
  7. Benito, C., Diaz, B. N., Jimenez–Aguado A. M. et al. (2011). Spiropiperidine compounds as orl–1 receptor antagonists. Pat. WO 2011/60217 A1. № PCT/US2010/056449; declared 12.11.2010; published 19.05.2011.
  8. Baraldi, P. G., Cacciari, B., Spalluto, G. et.al. (1997). A new synthetic approach to indazole synthesis. Synthesis, 10, 1140–1142. doi: 10.1055/s–1997–1328
  9. Sridhar, R., Perumal, P. T. (2005). A new protocol to synthesize 1,4–dihydro–pyridines by using 3,4,5–trifluorobenzeneboronic acid as a catalyst in ionic liquid: synthesis of novel 4–(3–carboxyl–1H–pyrazol–4–yl)–1,4–dihydropyridines. Tetrahedron, 61 (9), 2465–2470. doi: 10.1016/j.tet.2005.01.008
  10. Matiychuk, V. S., Potopnyc, M. A., Obushak, M. D. (2013). A simple and efficient synthesis of ethyl 1–aryl–4–formyl–1H–pyrazole–3–carboxylates. Journal of Heterocyclic Chemistry, 50 (1), E 43–E47. doi: 10.1002/jhet.1042
  11. Griffith, D. A., Dow, R. L., Bagley, S. W. et al. (2012). N1/n2–lactam acetyl–coa carboxylase inhibitors. Pat. US 2012/108619 A1. № 13/282,964; declared 29.10.2011; published 03.05.2012.
  12. Bratenko, M. K., Barus, M. M., Vovk, M. V. (2009). Khimiia geterotcyklicheskikh soedinenii, 45 (12), 1464–1468.
  13. Receveur, J. M., Bjurling, E., Murray, A. et al. (2009). Cannabinoid receptor modulators. Pat. WO 2009/74782 A1; declared 08.12.2008; published 18.06.2009.
  14. Carpio, P. A., Griffith, D. A., Sakya, S. et al. (2006). New bicyclic cannabinoid receptor–1 (CB1–R) antagonists. Bioorganic & Medicinal Chemistry Letters, 16 (3), 731–736. doi: 10.1016/j.bmcl.2005.10.019
  15. Sakia, S. M. (2004). Cannabinoid receptor ligands and uses thereof. Pat. WO 2004/99157 A1. № PCT/IB2004/001484; declared 29.04.2004; published 18.11.2004.
  16. Dymock, B. W., Gill, A. L., Jones, P. S. et al. (2003). Anti–HIV pyrazole derivatives. Pat. US 6538015. № 10/154,585; declared 24.05.2002; published 25.03.2003.
  17. Cooper, M., Receveur, J.–M., Hoegberg, T. et al. (2008). Pyrazole derivatives as modulators of cannabinoid receptor. Pat. WO 2008/74982 A1. № PCT/GB2007/004703; declared 10.12.2007; published 26.06.2008.
  18. Carpino, P., Dow, R. (2004). Cannabinoid receptor ligands and uses thereof. Pat. US 2004/214855 A1. № 10/823,107; declared 12.04.2004; published 28.10.2004.
  19. Dow, R., Carpino, P. (2006). Acylaminobicyclic heteroaromatic compounds and uses thereof. Pat. US 2006/241100 A1. № 11/409,458; declared 20.04.2006; published 26.10.2006.
  20. Furet, P., Guadnano, V., Holzer, P. et al. (2013). Pyrazolopyrrolidine compounds. Pat. WO 2013/80141 A1. № PCT/IB2012/056796; declared 28.11.2012; published 06.06.2013.
  21. Chaudhari, S. S., Gudade, G. B., Karnik, P. et al. (2009). PFused pyrazole derivatives as cannabinoid receptor modulators. at. WO 2009/95752 A1. № PCT/IB2009/000083; declared 20.01.2009; published 06.08.2009.
  22. Cheng, L. (2006). Therapeutic agents. Pat. WO 2006/67443 A1. № PCT/GB2005/004977; declared 21.12.2005; published 29.06.2006.
  23. Ito, M., Suzaki, T., Yamamoto, S. (2009). Substituted pyrazole derivatives. Pat. US 2009/270359 A1. №12/199,008; declared 30.12.2007; published 29.10.2009.
  24. Manfredini, S., Bazzanini, R., Baraldi, P. G. et al. (1996). Design, synthesis and antiproliferative activity of methyl–4–iodo–1–β–D–ribofuranosylpyrazole–3–carboxylate (IPCAR) and derivatives, against human leukemia, lymphomas and solid tumots cell lines in vitro. Medicinal Chemistry Research, 6 (5), 293–311.
  25. Manfredini, S., Baraldi, P. G., Bazzanini, R. et al. (1994). New Direct Glycosylation of Pyrimidine, Pyrazole, Imidazole and Purine Heterocycles via their N–tetrahydropyranyl (THP) Derivatives. Journal of the Chemical Society, Chemical Communications, 5, 583–584. doi: 10.1039/C39940000583
  26. Carpino, P., Sakya, S. (2004). Cannabinoid receptor ligands and uses thereof. Pat. US 2004/248881 A1. № 10/853,993; declared 25.05.2004; published 09.12.2004.
  27. Bratenko, M. K., Barus, M. M., Denisenko, O. M., Rodіk, R. V., Vovk, M. V., Yarosh, O. K. (2015). Zhurnal orhanichnoi ta farmatsevtychnoi khimii, 13 (1), 37–43.
  28. Keefe, A. D., Wagner, R. W., Clark M. et al. (2014). Benzhydrol–pyrazole derivatives having kinase inhibitory activity and uses thereof. Pat. WO 2013/106432 A1. № EP20130735755; declared 09.01.2013; published 19.11.2014.
  29. Cheng, L. (2006). Therapeutic agents. Pat. WO 2006/67443 A1. № PCT/GB2005/004977; declared 21.12.2005; published 29.06.2006.
  30. Okada, M., Hasumi, K., Nishimoto, T. et al. (2013). Heterocyclic compound and h1 receptor antagonist. Pat. US 2013/85127 A1. № 13/699,892; declared 23.05.2011; published 04.04.2013.
  31. Benito Collado, A. B., Buezo, N. D., Jimenez–Aguado, A. M. et al. (2011). Spiropiperidine compounds as orl–1 receptor antagonists. Pat. US 2011/118251 A1. № 12/943,187; declared 16.11.2009; published 19.05.2011.
  32. Wan, Y., Pan, S., Zhang, G. et al. (2009). Compounds and compositions as itpkb inhibitors. Pat. WO 2009/123948 A2. № PCT/US2009/038734; declared 30.03.2009; published 08.10.2009.
  33. Tanaka, Y., Aikava, K., Nishida, G. et al. (2013). Discovery of Potent Mcl–1/Bcl–xL Dual Inhibitors by Using a Hybridization Strategy Based on
  34. Structural Analysis of Target Proteins. Journal of Medicinal Chemistry, 56 (23), 9635–9645. doi: 10.1021/jm401170c
  35. Matiychuk, V. S., Potopnyc, M. A., Obushak, M. D. (2009). Synthesis and reactions of 3–(3–ethoxycarbonyl–1–phenyl–1H–pyrazol–4–yl)propenic
  36. acid. Russian Journal Organic Chemistry, 45 (5), 712–718. doi: 10.1134/S107042800905011X
  37. Toche, R. B., Bhavsar, D. C., Kazi, M. A. et al. (2010). Synthesis of pyrazolopyridine 3–carboxylates by Friedlander condensation. Journal of Heterocyclic Chemistry, 47 (2), 287–291. doi: 10.1002/jhet.294
  38. Vovk, M. V., Yarosh, O. K., Denysenko, O. M. et al. (2014). 5–[(1–aryl–3R–1H–pіrazol–4–іl)metylen]–2–tiokso1,3–tіazolіdyn–4–ony, yakі vyiavliaiut hіpohlіkemіchnu aktyvnіst. Patent na korysnu model № 92648. № declared 01.04.2014; published 26.08.2014.
  39. Bratenko, M. K., Barus, M. M., Vovk, M. V. (2013). Khimiia geterotcyklicheskikh soedinenii, 48 (10), 1545–1549.
  40. Dunn, J. P., Hogg, J. H., Mirzadegan, T. et al. (2008). Non–nucleoside reverse transcriptase inhibitors. Pat. EP. 1988081 A1. № 20070713881; declared 06.02.07; published 05.11.08.
  41. Wan, Y., Pan, S., Zhang, G. et al. (2004). Compounds and compositions as itpkb inhibitors. Pat. WO 2004/74257 A1. № PCT/EP2004/001477; declared 17.02.04; published 02.09.04.
  42. M. K. Bratenko, M. M. Barus, D. V. Rotar et al. (2015). Naukovyi vіsnyk Chernіvetskoho unіversytetu, 753, 15–21.
  43. Carpino, P. A., Sakya, S. M. (2005). Bicyclic pyridazinone cannabinoid receptor ligands and uses thereof. Pat. WO 2005/61504 A1. № PCT/EP2004/001477; declared 06.12.04; published 07.07.05.
  44. Baraldi, P. G., Manfredini, S., Romagnoli, R. et al. (1998). Synthesis and Anti–HSV–1 Activity of 6 Substituted Pyrazolo[3,4–d]Pyridazin–7–one. Nucleosides. Nucleosides, Nucleotides and Nucleic Acids, 17 (12), 2165–2173. doi: 10.1080/07328319808004307
  45. Bratenko, M. K., Barus, M. M., Vovk, M. V. (2013). Polyfunctional pyrazoles. 8*. Synthesys of 6–alkyl–2–aryl–2H–pyrazolo[4,3–d]pyrimidine–5,7(4H,6H)–diones based on ethyl 1–aryl–4–isocyanatopyrazole–3–carboxylates. Chemistry of Heterocyclic Compounds, 49 (9), 1345–1351. doi:
  46. 1007/s10593–013–1383–1

Downloads

Published

2017-12-14

How to Cite

(1)
Bratenko, M. K.; Barus, M. M.; Vovk, M. V. Esters of 4-Formylpyrazol-3-Carboxylic Acids. J. Org. Pharm. Chem. 2017, 15, 3-20.

Issue

Vol. 15 No. 4(60) (2017)

Section

Original Researches

License

Copyright (c) 2017 National University of Pharmacy

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Authors publishing their works in the Journal of Organic and Pharmaceutical Chemistry agree with the following terms:

1. Authors retain copyright and grant the journal the right of the first publication of the work under Creative Commons Attribution License allowing everyone to distribute and re-use the published material if proper citation of the original publication is given.

2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal’s published version of the work (e.g., post it to an institutional repository or publish it in a book) providing proper citation of the original publication.

3. Authors are permitted and encouraged to post their work online (e.g. in institutional repositories or on authors’ personal websites) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (see The Effect of Open Access).