STEREOCHEMISTRY OF THE [3+2] CYCLOADDITION OF ACRYLONITRILE TO THE N-OXIDE OF 5-METHYL-4,5-DIHYDRO-3H-SPIRO[BENZ-2-AZEPINE-3,1'-CYCLOHEXANE]

Authors

  • А. В. Варламов Russian Peoples Friendship University, Moscow 117927
  • Ф. И. Зубков Russian Peoples Friendship University, Moscow 117927
  • K. Ф. Турчин Center for Drug Chemistry, All-Russian Pharmaceutical Chemistry Research Institute, Moscow 119815
  • А. И. Чернышев Russian Peoples Friendship University, Moscow 117927
  • P. C. Борисов Russian Peoples Friendship University, Moscow 117927

Keywords:

alkenes, benz-2-azepines, spiro compounds, cyclic nitrones, [3+2] cycloaddition

Abstract

The [3+2] cycloaddition of acrylonitrile to the N-oxide of 5-methyl-4,5-dihydro-3H-spiro[benz-2-azepine-3,1'-cyclohexane] under conditions of both kinetic and thermodynamic control proceeds without regioselectivity or stereoselectivity with the formation of eight isomeric 1-cyano- and 2-cyano-7-methyl-1,2,4,6,7,11b-hexahydro-5H-spiro[isoxazolidino[3,2-a]benz-2-azepine-5,1'-cyclohexanes], six of which were isolated in an individual state. Their structure and stereochemistry were established by 1H NMR.

How to Cite
Varlamov, A. V.; Zubkov, F. I.; Turchin, K. F.; Chernyshev, A. I.; Borisov, R. S. Chem. Heterocycl. Compd. 2001, 37, 1244. [Khim. Geterotsikl. Soedin. 2001, 1360.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1013853728211

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Published

2001-10-25

Issue

No. 10 (2001)

Section

Original Papers