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An alternative synthesis of 3‐amino‐1,2,3,4‐tetrahydrocarbazoles
Author(s) -
Bird C. W.,
Wee A. G. H.
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220146
Subject(s) - chemistry , azide , toluene , combinatorial chemistry , organic chemistry
3‐Amino‐1,2,3,4‐tetrahydrocarbazoles are easily prepared from the readily available 3‐hydroxy‐1,2,3,4‐tetrahydrocarbazoles by conversion of the latter to the p ‐toluene‐ or methanesulfonate ester, followed by nu‐cleophilic displacement with azide ion. The resulting 3‐azido‐1,2,3,4‐tetrahydrocarbazoles are then catalytically hydrogenated to their 3‐amino counterparts.