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Reactions of N- and C-Alkenylanilines: V. Synthesis of Iodo-Substituted Heterocycles from o-Cycloalkenylanilines and Their Transformations

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Abstract

Iodination of N-isopropyl- and N-benzyl-2-(2-cyclohexenyl)anilines gave the corresponding 1-iodo-hexahydrocarbazoles which underwent quantitative isomerization into 3-iodo-2,4-propano-1,2,3,4-tetrahydro-quinolines. Nucleophilic substitution in 1-iodohexahydrocarbazoles and 3-iodo-2,4-propano-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole was studied. N-Allylation of the latter via reaction with allyl bromide is accompanied by replacement of the iodine atom by bromine.

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Authors
  1. R. R. Gataullin
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  2. F. F. Minnigulov
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  3. L. V. Spirikhin
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  4. I. B. Abdrakhmanov
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Gataullin, R.R., Minnigulov, F.F., Spirikhin, L.V. et al. Reactions of N- and C-Alkenylanilines: V. Synthesis of Iodo-Substituted Heterocycles from o-Cycloalkenylanilines and Their Transformations. Russian Journal of Organic Chemistry 40, 986–991 (2004). https://doi.org/10.1023/B:RUJO.0000045190.75301.70

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  • DOI: https://doi.org/10.1023/B:RUJO.0000045190.75301.70

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