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Synthesis of novel 5‐hydroxy‐3‐alkoxy‐ and 5‐hydroxy‐3‐alkylthioindole‐2‐carboxamides
Author(s) -
Unangst Paul C.,
Connor David T.,
Miller Steven R.
Publication year - 1996
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.5570330614
Subject(s) - chemistry , alkoxy group , amide , indole test , carboxamide , protecting group , organic chemistry , combinatorial chemistry , alkyl
The preparation of several novel 5‐hydroxyindole‐2‐carboxamides is described. A 5‐benzyloxyindole ester was elaborated to the 3‐bromo, 3‐hydroxy, and 3‐alkoxy ester intermediates followed by conversion to the amide and debenzylation. A related 5‐acetyloxy indole ester was converted to 3‐sulfinyl and 3‐alkylthio intermediates before simultaneous amidation and removal of the 5‐hydroxy protecting group.