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Reactions of N- and C-alkenylanilines: VIII. Synthesis of functionalized cycloalka[b]indoles from o-(cycloalk-2-en-1-yl)anilines

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Abstract

N-Acyl-2-(cyclohex-2-en-1-yl)anilines react with molecular iodine to give the corresponding N-acyl-1-iodo-1,2,3,4,4a,9a-hexahydrocarbazoles which undergo isomerization into 1-R-2a,3,4,5,5a,10a-hexahydro[1,3]oxazolo[5,4,3-j,k]carbazol-10-ium iodides; no isomerization occurs with N-acetyl-3-iodo1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole. The reaction of N-p-tolylsulfonyl-3,4,4a,9a-tetrahydrocarbazoles with hydrogen peroxide leads to the formation of a single 1,2-epoxy derivative with trans orientation of the nitrogen-and oxygen-containing rings. N-p-Tolylsulfonyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles give rise to the corresponding 2,3-epoxy derivatives with both trans and cis orientation of the dihydropyrrole and oxirane fragments. The resulting epoxides undergo trans-opening with formation of N-p-tolylsulfonyl-1-hydroxy-2-methoxy-1,2,3,4,4a,9a-hexahydrocarbazoles and N-p-tolylsulfonyl-3-hydroxy-2-methoxy-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles on heating in methanol in the presence of KU-2 cation exchanger. Mutual orientation of the oxirane and nitrogen-containing rings in the epoxides derived from cyclopenta[b]-indoles was proved by X-ray analysis.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    R. R. Gataullin, N. A. Likhacheva & I. B. Abdrakhmanov

  2. Nesmeyanov Institute of Organometallic Compounds, Russian Academy of Sciences, Moscow, Russia

    K. Yu. Suponitskii

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  1. R. R. Gataullin
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  2. N. A. Likhacheva
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  3. K. Yu. Suponitskii
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  4. I. B. Abdrakhmanov
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Correspondence to R. R. Gataullin.

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Original Russian Text © R.R. Gataullin, N.A. Likhacheva, K.Yu. Suponitskii, I.B. Abdrakhmanov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 9, pp. 1316–1326.

For communication VII, see [1].

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Gataullin, R.R., Likhacheva, N.A., Suponitskii, K.Y. et al. Reactions of N- and C-alkenylanilines: VIII. Synthesis of functionalized cycloalka[b]indoles from o-(cycloalk-2-en-1-yl)anilines. Russ J Org Chem 43, 1310–1321 (2007). https://doi.org/10.1134/S1070428007090096

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  • DOI: https://doi.org/10.1134/S1070428007090096

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