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The reaction of indole and the indole grignard reagent with phosgene. A facile synthesis of indole‐3‐carboxylic acid derivatives
Author(s) -
Bergman Jan,
Carlsson René,
Sjöberg Birger
Publication year - 1977
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.5570140701
Subject(s) - phosgene , chemistry , oxalyl chloride , indole test , reagent , organic chemistry , glyoxylic acid , chloride , carboxylic acid , combinatorial chemistry , medicinal chemistry
Indole‐3‐carboxylic acid (as well as indole‐3‐glyoxylic acid) derivatives are readily prepared from indoles (including oxindoles) and phosgene (oxalyl chloride), respectively. The interaction of these reagents with the indole Grignard reagent afforded several products including the cyclo‐tetramers, 21 and 30 . Indolo‐fused heterocycles can be readily prepared from the reaction of phosgene (or oxalyl chloride) with suitable reactants. Thus e.g. , phosgene and 2‐(2‐hydroxy‐phenyl)‐ N ‐methylindole readily gave 5,6‐dihydro‐11‐methyl‐6‐oxobenzo[ a ]pyrano[4,3‐ b ] indole ( 33 ).