Preparation of 4,4a,9,9a-tetrahydrocarbazoles and 1,3a,4,8b-tetra- hydrocyclopenta[b]indoles

被引：0
|
作者：
Gataullin R.R. [1 ]
Ishberdina R.R. [1 ]
Shitikova O.V. [1 ]
Minnigulov F.F. [1 ]
Spirikhin L.V. [1 ]
Abdrakhmanov I.B. [2 ]
机构：
[1] Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences
[2] Bashkir State Agricultural University
来源：
Chemistry of Heterocyclic Compounds | 2006年 / 42卷 / 8期
关键词：
Conformation; Cyclopenta[b]indolines; Dehydroiodination; Halocyclization; Hexahydrocarbazoles; Tetrahydrocarbazoles;
D O I：
10.1007/s10593-006-0199-7
中图分类号：
学科分类号：
摘要：
Halocyclization of mesylates or tosylates of 2-(cycloalk-2-en-1-yl)anilines gives N-methanesulfonyl-or N-toluenesulfonyl-1-halo-1,2,3,4,4a,9a- hexahydrocarbazoles, heating of which in DMF at 160°C or in piperidine at 110°C leads to 4,4a,9,9a-tetrahydro-3H-carbazoles. Heating N-methanesulfonyl-1-iodo-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole in DMF at 180-200°C gives 1,3a,4,9b-tetrahydrocyclopenta[b]indole, while in the presence of an ortho-methyl substituent the dehydroiodination reaction proceeds in piperidine at 110°C in high yield. The effect of the nature of the ortho substituent of N-methyl-1-iodo-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole on the conformational equilibrium of the cyclopentane ring has been established by 1H NMR spectroscopy. © 2006 Springer Science+Business Media, Inc.
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页码：1025 / 1031
页数：6
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