[3+2] CYCLOADDITION OF DIMETHYL ACETYLENEDICARBOXYLATE, METHYL ACRYLATE, AND ETHYL ACRYLATE TO 4,5-DIHYDRO-5-METHYL-3H-SPIRO[BENZ-2-AZEPINE-3,1'-CYCLOHEXANE] N-OXIDE

Authors

  • А. В. Варламов Russian People's Friendship University, Moscow 117198
  • А. И. Чернышев Russian People's Friendship University, Moscow 117198
  • Ф. И. Зубков Russian People's Friendship University, Moscow 117198
  • К. Ф. Турчин Pharmaceutical Chemical Center, All-Russian Pharmaceutical Chemistry Institute, 119815 Moscow
  • А. Н. Левов Russian People's Friendship University, Moscow 117198

Keywords:

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

Abstract

The cycloaddition of methyl acrylate and ethyl acrylate to 4,5-dihydro-5-methyl-3H-spiro[benz-2-azepine-3,1'-cyclohexane] N-oxide proceeds without either regiospecificity or stereospecificity. Eight geometrical isomers of spiro[isoxazolidino[3,2-a]benz-2-azepine-5,1'-cyclohexane] were formed, of which several were isolated as pure samples. The cycloaddition of dimethyl acetylenedicarboxylate proceeds stereoselectively, leading to spiro[isoxazolino[3,2-a]benz-2-azepine-5,1'-cyclohexane] with cis arrangement of the protons at C(7) and C(11b).

How to Cite
Varlamov, A. V.; Chernyshev, A. I.; Zubkov, F. I.; Turchin, K. F.; Levov, A. N. Chem. Heterocycl. Compd. 2004, 40, 364. [Khim. Geterotsikl. Soedin. 2004, 447.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000028634.08685.99

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Published

2004-03-25

Issue

No. 3 (2004)

Section

Original Papers