CYCLOADDITION OF NITRONES TO 1,3-DIARYLPROPENONES AND SUBSEQUENT TRANSFORMATIONS OF THE RESULTING ISOXAZOLIDINES

Authors

  • Екатерина В. Сироткина Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034
  • Мария М. Ефремова Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034
  • Галина Л. Старова Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034
  • Михаил А. Кузнецов Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034
  • Александр П. Молчанов Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034

DOI:

https://doi.org/10.1007/5707

Keywords:

chalcones, isoxazolidines, nitrones, 1, 3-dipolar cycloaddition, reduction

Abstract

Ketonitrones containing two ester groups react regio- and stereoselectively with 1,3-diarylpropenones to form isoxazolidines with ester groups at position 3 of the ring. The action of zinc in acetic acid on these isoxazolidines causes opening of the ring with the formation of 3-amino alcohols, the subsequent cyclization of which leads to polysubstituted lactones. Reduction of the benzoyl group of isoxazolidine with sodium borohydride leads, as a result of subsequent transformations, to the formation of substituted 1,3,4-triaryl-6-oxodihydro-1H,3H-furo[3,4-c]isoxazole-6a(6H)-carboxylates as single diastereomers.

Authors: Ekaterina V. Sirotkina, Mariia M. Efremova, Galina L. Starova, Mikhail A. Kuznetsov, Alexander P. Molchanov*

Author Biographies

Екатерина В. Сироткина, Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034

кафедра органической химии, аспирант

Мария М. Ефремова, Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034

кафедра органической химии, ассистент, к.х.н.

Галина Л. Старова, Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034

Институт химии

Михаил А. Кузнецов, Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034

д.х.н., зав.кафедрой органической химии

Александр П. Молчанов, Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034

доктор химических наук, зав. лабораторией химии карбенов и родственных интермедиатов

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Published

2020-10-14

Issue

Vol. 56 No. 9 (2020)

Section

Original Papers