SYNTHESIS OF 4,5-DIHYDROISOXAZOLE DERIVATIVES OF MALEOPIMARIC ACID BY 1,3-DIPOLAR CYCLOADDITION REACTION BETWEEN ITS ALLYL DERIVATIVES AND AROMATIC NITRILE OXIDES

Authors

  • Гузэль Ф. Вафина Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054
  • Альфия А. Мухамедьянова Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054
  • Марина Д. Ханова Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054
  • Леонид В. Спирихин Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

DOI:

https://doi.org/10.1007/4627

Keywords:

4, 5-dihydroisoxazoles, maleopimaric acid, nitrile oxides, 1, 3-dipolar cycloaddition

Abstract

While searching for pharmacologically active compounds among 4,5-dihydrooxazole derivatives of maleopimaric acid, we studied for the first time the reaction between allyl-substituted maleopimaric acid derivatives and aromatic nitrile oxides that were generated from oximes by oxidation with sodium hypochlorite with or without ultrasonication of the biphasic system. The reaction occurred under mild conditions and regiospecifically provided 4,5-dihydroisoxazol-5-ylmethyl derivatives of maleopimaric acid in 77–99% yields.

Authors: Guzel F. Vafina*, Alfiya A. Mukhamed'yanova, Marina D. Khanova, Leonid V. Spirikhin

Author Biographies

Гузэль Ф. Вафина, Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

Гузэль Фагимовна Вафина

кандидат химичесих наук, старший научный сотрудник лаборатории Биоорганической химии и катализа

Альфия А. Мухамедьянова, Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

магистрант

Марина Д. Ханова, Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

Марина Дамировна Ханова

кандидат химических наук, научный сотрудник лаборатории Биоорганической химии и катализа

Леонид В. Спирихин, Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

Леонид Васильевич Спирихин

кандидат химических наук, заведующий лабораторией Физико-химических методов анализа

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Published

2018-10-01

Issue

Vol. 54 No. 8 (2018)

Section

Original Papers