TANDEM REACTIONS OF THERMOLYSIS AND [3+2] CYCLOADDITION IN THE SYNTHESIS OF 3-HETARYL-4-NITROFUROXANS FROM 4-NITROFUROXANNITROLIC ACID

Authors

  • Александр А. Ларин N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Леонид Л. Ферштат N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Нина Н. Махова N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia

DOI:

https://doi.org/10.1007/5620

Keywords:

nitrofuroxans, nitrolic acids, 1, 2, 5-oxadiazoles, cycloaddition, regioselectivity.

Abstract

A tandem method of synthesis of 3-hetaryl-4-nitrofuroxans was developed based on the one-pot sequence of thermolysis of 4-nitrofuroxannitrolic acid to the corresponding 4-nitro-3-furoxancarbonitrile oxide and [3+2] cycloaddition of the latter to acetylenes and olefins. It was established that the synthesized 3-(isoxazol-3-yl)- and 3-(isoxazolin-3-yl)-4-nitrofuroxans are formed with high regioand diastereoselectivity.

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Published

2020-05-28

Issue

Vol. 56 No. 5 (2020)

Section

Short Communications