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Brønsted Acid‐Promoted Sequential Hydroarylation– Hydroamidation of Arene‐Tethered 1‐(2‐Alkynylphenyl)ureas: Direct Access to 4,4‐Spiro‐3,4‐dihydro‐2‐(1 H )‐quinazolinones
Author(s) -
Wang Honggen,
Zhao Jiaji,
Zhang Jiancun,
Zhu Qiang
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100223
Subject(s) - chemistry , intramolecular force , moiety , protonation , brønsted–lowry acid–base theory , sulfur , urea , medicinal chemistry , carbon fibers , nitrogen , combinatorial chemistry , catalysis , stereochemistry , organic chemistry , ion , materials science , composite number , composite material
A Brønsted acid‐promoted approach to 4,4‐sipro‐3,4‐dihydro‐2‐(1 H )‐quinazolinones from arene‐tethered 1‐(2‐alkynylphenyl)ureas has been developed. The reaction is initiated by intramolecular hydroarylation followed by hydroamidation, assisted by intramolecular proton transfer from the protonated urea moiety. A variety of tethering atoms, including carbon, oxygen, sulfur, and protected nitrogen are compatible with the reaction conditions.