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Carbonylation of Anthranilic Acid with Aryl and Heteroaryl Bromides to Synthesize Benzoxazinone Derivatives
Author(s) -
Chavan Sujit P.,
Bhanage Bhalchandra M.
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600253
Subject(s) - chemistry , anthranilic acid , aryl , bromide , carbonylation , organic chemistry , catalysis , combinatorial chemistry , alkyl , carbon monoxide
A simple and efficient, PdCl 2 (PhCN) 2 /P( t Bu) 3 ⋅HBF 4 ‐catalyzed carbonylative cyclization of anthranilic acid with aryl bromide was investigated for the synthesis of benzoxazinones under mild reaction conditions. The developed protocol has been extended for the synthesis of quinazolin‐4(3 H )‐ones. Furthermore, the tolerance of a wide range of functional groups on anthranilic acid as well as on aryl bromide demonstrates the practical utility of the protocol.