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Synthesis of novel 1‐phenyl‐1 H ‐indole‐2‐carboxylic acids. II. Preparation of 3‐dialkylamino, 3‐alkylthio, 3‐alkylsulfinyl, and 3‐alkylsulfonyl derivatives
Author(s) -
Unangst Paul C.,
Connor David T.,
Stabler S. Russell
Publication year - 1987
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.5570240353
Subject(s) - chemistry , indole test , thionyl chloride , reagent , aryl , medicinal chemistry , bromobenzene , alkyl , organic chemistry , chloride , catalysis
The synthesis of novel indole‐2‐carboxylic acids with amino‐ and sulfur‐containing substituents in the indole 3‐position is described. An Ullmann reaction with bromobenzene converted 1 H ‐indoles with 3‐(acetylamino)‐ and 3‐(diethylamino)‐substituents into 1‐phenyl‐1 H ‐indoles. Reaction of 3‐unsubstituted indoles with thionyl chloride provided indole 3‐sulfinyl chlorides, which reacted with alkyl and aryl Grignard reagents to form the corresponding sulfoxides. The indole sulfoxides thus obtained were reduced to sulfides or oxidized to sulfones.