Reactions of N- and C-alkenylanilines: VIII. Synthesis of functionalized cycloalka[b]indoles from o-(Cycloalk-2-en-1-yl)anilines
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-iodo-1,2,3...
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Published in | Russian journal of organic chemistry Vol. 43; no. 9; pp. 1310 - 1321 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
NEW YORK
Springer Nature
01.09.2007
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Subjects | |
Online Access | Get full text |
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Summary: | 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-iodo-1,2,3,3a,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]lndoles 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-hexahydrocarbazoics and N-p-tolysulfonyl-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 nitro-en-containina rin-s in the epoxides derived from cyclopenta[b]indoles was proved by X-ray analysis. |
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ISSN: | 1070-4280 1608-3393 |
DOI: | 10.1134/S1070428007090096 |