The synthesis and reactions of diacethyl(dialkoxycarbonyl) substituted hydroxycyclohexanones / A.I.Ismiyev, A.M.Maherramov, V.A.Sukach, M.V.Vovk

A. I. Ismiyev, A. M. Maherramov, V. A. Sukach, M. V. Vovk

Abstract


The literature sources concerning the importance of diacetyl (dialkoxycarbonyl) substituted hydroxycyclohexanones as highly functionalized carbocyclic compounds, on the one hand, as well as, on the other hand, the research prospects in the field of synthetic methods development based on these compounds for obtaining various heterocyclic systems have been generalized and systematized. It has been noted that the main method of the synthesis for diacetyl (diethoxycarbonyl) cyclohexanolones is diketone condensation of acetylacetone or ethyl acetoacetate with aldehydes in the presence of catalytic amounts of piperidine. An important useful peculiarity of this approach is a variation of the initial reagents, allowing modification of the substituents in a wide range. However, the dependence of selectivity and regiodirection of the reaction on various factors makes the studies in this area quite interesting and not always predictable. The phenomenon of keto-enol tautomerism of diacetyl substituted cyclohexanolones and factors that control stability of their enol form have been discussed. It has been concluded that reactions of these multicarbonyl compounds with ambident nitrogen-containing nucleophilic reagents are efficacious for the synthesis of new biologically promising representatives of carbofused heterocycles, such as isoxazoles, pyrazoles, triazolo[3,4-b] quinazolines, thieno[2,3-c]isoquinolines and pyrazolo[3,4-c]isoquinolines. The importance of oxidation, dehydration and aromatization processes of hydroxycyclohexanones for organic synthesis has been emphasized.


Keywords


cyclohexanolones; diketone condensation; tautomerism; annulation; dehydration; aromatization

References


Kriven’ko A. P., Sorokin V. D. Russ. J. Org. Chem., 1999, Vol. 35, No.8, pp.1097-1112.

Sorokin V. V., Diss. dokt. khim. nauk, Saratov, 2004, 305 p.

Hote B. S., Lokhande P. D. Synt. Commun., 2014, Vol. 44, No.10, pp.1492-1500.

Sorokin V. V., Ramazanov A. K., Kriven’ko A. P. Izvestiya Vysshikh uchebnykh zavedeniy. Khimiia i khimicheskaya tekhnologiya, 2002, Vol. 45, No.6, pp.129-134.

Rehberg R., Krohnke F. Lieb. Ann. 1968, Bd. 717, pp.91-95.

Petkov I., Ojilova A., Markov P. Monatsh. Chem., 1990, Vol. 121, No.1, pp.85-88.

Aliyev Z. G., Gein V. L., Nosova N. V., Potemkin K. D., Krivenko A. P. Russ. J. Org. Chem., 2006, Vol. 42, No.9, pp.1411-1413.

Gein V. L., Levandovskaya E. V., Nosova N. V., Antonova N. V., Voronina E. V., Vakhrin M. I., Kriven’ko A. P. Pharm. Chem. J., 2007, Vol. 41, No.12, pp.643-645.

Subbotin V. E., Sorokin V. V., Golikov A. G., Kriven’ko A. P. Russ. J. Org. Chem., 2010, Vol. 46, No.4, pp.594-596.

Sargsyan M. S., Hayotsyan S. S.,Khachaturyan A. Kh., Badasyan A. E., Panosyan G. A.,Konkova S. G. Chem. Heterocycl. Comp., 2013, Vol. 48, No.12, pp.1805-1808.

Sorokin V. V. Izvetiya Saratovskoho universiteta. Seriya Khimiya, Biologiya, Ekologiya, 2007, Vol. 7, pp.42-46.

Morozova A. A. Diss. kand. khim. nauk, Saratov, 2008, 160 p.

Nitta H., Tahimoto K., Ueda I. Chem. Pharm. Bull., 1992, Vol. 40, No.4, pp.858-863.

Kingsbury C. A., Richard S. E., Perun T. J. J. Org. Chem., 1970, Vol. 35, No.9, pp.2913-2918.

Stanley J., Kingsbury C. A. J. Org. Chem., 1986, Vol. 51, No.13, pp.2539-2544.

Sorokin V. V., Kriven’ko A. P., Ramazanov A. K. Russ. Chem. Bull., 2004, Vol. 53, No.12, pp.2782-2786.

Ramazanov A. K., Diss. kand. khim. nauk, Saratov, 2003, 128 p.

Grigir’eva E. A., Komintern E. A., Kriven’ko A. P., Sorokin V. V. Khimiya i kompyuternoe modelirivaniye. Butlerovskiye soobscheniya, 2004, Vol. 5, No.2, pp.59-63.

Subbotin V. E., Torgashin E. M., Ramazanov A. K., Sorokin V. V. Sovremennye problemy teoreticheskoy i eksperimental’noy khimiyi. Saratov, 2007, p.147.

Subbotin V. E., Sorokin V. V. Problemy teoreticheskoy i eksperimental’noy khimiyi, Ekaterinburg, 2007, p.319.

Sorokin V. V., Grogor’ev A. V., Ramazanov A. K., Kriven’ko A. P. Russ. J. Org. Chem., 2000, Vol. 36, No.6, pp.781-784.

Ramazanov A. K., Sorokin V. V., Kriven’ko A. P. Khimiya i kompyuternoe modelirivaniye. Butlerovskiye soobscheniya, 2002, No.6, pp.79-84.

Sorokin V. V., Kriven’ko A. P., Vinogradova N. A., Plotnikov O. P. Khim.-Farm. Zhurn., 2001, Vol. 35, No.9, pp.24-25.

Shchelochkova O. A., Sorokin V. V., Kriven’ko A. P. Khimiya i kompyuternoe modelirivaniye. Butlerovskiye soobscheniya, 2003, No.1, pp.20-22.

Shchelochkova O. A., Diss. kand. khim. nauk, Saratov, 2006, 167 p.

Krivenko A. P., Kozlova E. A., Grigorev A. V., Sorokin V. V. Molecules, 2003, Vol. 8, No.2, pp.251-255.

Maharramov A. M., Ismiyev A. I., Rashidov B. A. Acta Cryst. Sect. E, 2011, Vol. 67, p.o187.

İsmiev A. İ., Rashidov B. A., Aliyev İ. A. Azerb. Chem. J., 2011, No.2, pp.73-77.

Ismiyev A. I., Maharramov A. M., Aliyeva R. A., Asketov R. K., Makhmudov K. T., Kopylovich M. N., Naili H., Pombeiro J. L. J. Mol. Struct., 2013,

Vol. 1032, pp.83-87.

Gein V. L., Nosova N. V., Potemkin K. D., Aliyev Z. G., Kriven’ko A. P. Russ. J. Org. Chem., 2005, Vol. 41, No.7, pp.1016-1022.

Rajanarendar E., Rao K. E., Karunakar D. Ind. J. Chem. B., 2006, Vol. 45, No.3, pp.805-807.

Maharramov A. M., Ismiyev A. I., Rashidov B. A., Askerov R. K., Khrustalev V. N. Acta Cryst. Sect. E., 2011, Vol. 67, p.o1127.

Maharramov A. M., Ismiyev A. I., Rashidov B. A. News of Baku university. Series of natural sciences, 2011, No.1, p.35.

Ismiyev A. I., Maharramov A. M., Rashidov B. A., Mammadova G. Z., Askerov R. K. Acta Cryst. Sect. E., 2011, Vol. 67, p.o3018.

Maharramov A. M., Ismiyev A. I., Rashidov B. A. Acta Cryst. Sect. E., 2011, Vol. 67, p.m786.

Maharramov A. M., Ismiyev A. I., Rashidov B. A. News of Baku university. Series of natural sciences, 2011, No.4, p.22.

Gulai T. V., Golikov A. G. Russ. J. Org. Chem., 2012, Vol. 48, No.4, pp.613-615.

Poplevina N. V., Kuznetsova A. A., Kriven’ko A. P. Chem. Heterocycl. Comp., 2010, Vol. 46, No.9, pp.1148-1150.

Dyachenko V. D., Sukach S. M., Dyachenko A. D., Zubatyuk R. I., Shishkin O. V. Russ. J. Gen. Chem., 2010, Vol. 80, No.10, pp.2037-2042.

Sukach S. M., Dyachenko V. D. Russ. J. Org. Chem., 2015, Vol. 51, No.7, pp.1020-1025.

Dyachenko V. D., Sukach S. M. Russ. J. Gen. Chem., 2012, Vol. 82, No.2, pp.305-309.

Sukach S. M., Dyachenko V. D. Russ. J. Org. Chem., 2015, Vol. 51, No.6, pp.903-905.

Dyachenko V. D., Sukach S. М., Dyachenko A. D. Chem. Heterocycl. Comp., 2015, Vol. 51, No.1, pp.51-55.

Poplevina N. V., Kriven’ko A. P., Shchelochkova O. A., Golikova A. G., Solodovnikov S. F. Russ. J. Org. Chem., 2009, Vol. 45, No.12, pp.1790-1794.

Lopez A. F. J., Mendoza P. G., Benitez F. Z., Gonzalez F. S. An. Real. Soc. Esp. Quim., 1984, Vol. 80C, p.83.

Niwas S., Kumar S., Bhaduri A. Indian J. Chem. B., 1984, Vol. 23, No.7, pp.599-602.

Ismiyev A. I., Rashidov B. A., Allakhverdiyev M. A. Azerb. Chem. J., 2007, No.3, p.115.

Lopez A. F. J., Mendoza P. G., Benitez F. Z.,Gonzalez F. S. An. Real. Soc. Esp. Quim., 1985, Vol. 81C, p.5.

Grigor’eva E. Diss. kand. khim. nauk, Saratov, 1990, 139p.

İsmiyev A. İ., Maharramov A. M., Askerov R. K., Potekhin K. A. J. Struct. Chem., 2015, Vol. 56, No.6, pp.1209-1211.

İsmiyev A. İ. News of Baku university. Series of natural sciences, 2013, No.3, p.22.

Zinina E. A., Poplevina N. V., Sorokin V. V. Chem. Heterocycl. Comp., 2012, Vol. 48, No.10, pp.1562-1564.

Sharma A., Pandey J., Tripathi R. P. Tetrahedron Lett., 2009, Vol. 50, No.16, pp.1812- 1816.


GOST Style Citations






DOI: https://doi.org/10.24959/ophcj.16.905

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

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)