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2‐Indolyl ketone synthesis
Author(s) -
Unangst Paul C.,
Brown Richard E.,
Fabian Arthur,
Fontseré Frank
Publication year - 1979
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.5570160409
Subject(s) - chemistry , sulfone , carbanion , ketone , reactivity (psychology) , organic chemistry , indole test , alkyl , derivative (finance) , alkylation , medicinal chemistry , catalysis , medicine , alternative medicine , pathology , financial economics , economics
The preparation of 2‐indolyl alkyl ketones by reductive cleavage of a β‐keto sulfone or by the reaction of 1‐chloro‐2‐propanone (chloroacetone) with a 2‐aminobenzoic acid derivative is described. The β‐keto sulfone intermediates are prepared by condensation of the carbanion of dimethyl sulfone and indole‐2‐carboxylic acid esters. Lack of reactivity of several 2‐aminobenzoic acids in the 1‐chloro‐2‐propanone process is related to the presence of electron‐withdrawing substituents in the aromatic ring.