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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]

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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.

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Authors and Affiliations

  1. Russian Peoples Friendship University, Moscow, 117927

    A. V. Varlamov, F. I. Zubkov, A. I. Chernyshev & R. S. Borisov

  2. Center for Drug Chemistry, All-Russian Pharmaceutical Chemistry Research Institute, Moscow, 119815

    K. F. Turchin

Authors
  1. A. V. Varlamov
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  2. F. I. Zubkov
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  3. K. F. Turchin
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  4. A. I. Chernyshev
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  5. R. S. Borisov
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Varlamov, A.V., Zubkov, F.I., Turchin, K.F. et al. 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]. Chemistry of Heterocyclic Compounds 37, 1244–1250 (2001). https://doi.org/10.1023/A:1013853728211

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