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Copper‐Catalyzed Intramolecular C–C Bond Cleavage To Construct 2‐Substituted Quinazolinones
Author(s) -
Hu BenQuan,
Wang LiXia,
Yang Luo,
Xiang JunFeng,
Tang YaLin
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500473
Subject(s) - chemistry , intramolecular force , bond cleavage , cleavage (geology) , aryl , catalysis , stereochemistry , alkyl , copper , medicinal chemistry , combinatorial chemistry , organic chemistry , geotechnical engineering , fracture (geology) , engineering
Abstract An efficient method for a copper‐catalyzed intramolecular C–C bond cleavage to construct 2‐substituted quinazolinones has been developed. The C–C bond at the 2‐position of 2,2‐disubstituted‐1,2,3,4‐tetrahydroquinazolinone was selectively cleaved by a Cu/air catalytic system. The trend for the cleavage was dependent on the leaving group in the order of: alkyl > methyl > phenyl > substituted aryl. The process described herein provides an explanation for the mechanism of the reaction between substituted 2‐halobenzamides and α‐substituted arylmethanamines to construct 2‐substituted quinazolinones, which were previously reported and limited to the construction of 2‐arylquinazolinones.