New synthesis of 9-methanesulfonyl-1,2,3,9a-tetrahydro- and 1,2,3,4-tetrahydrocarbazoles from N-methanesulfonyl-2-(cyclohex-1-enyl)aniline
Mendeleev Communications Pub Date: DOI: 10.1070/MC2003v013n05ABEH001699
Abstract
The reaction of N-methanesulfonyl-2-(cyclohex-1-en-1-yl)aniline with Br2 in the presence of NaHCO3 in MeCN results in N-methanesulfonyl-2-(6-bromocyclohex-1-en-1-yl)aniline, which was cyclised to 9-methanesulfonyl-1,2,3,4-tetrahydrocarbazole, and the effect of NH3 leads to 9-methanesulfonyl-1,2,3,9a-tetrahydrocarbazole. The reaction of the latter with molecular bromine in the presence of pyridine results in 1-(9-methanesulfonyl-1,2,3,4-tetrahydro-4-carbazolyl)pyridinium bromide in a good yield.
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Journal Name：Mendeleev Communications
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CAS no.: 89640-58-4
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