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Iodine‐Catalyzed, Stereo‐ and Regioselective Synthesis of 4‐Arylidine‐4 H ‐benzo[ d ][1,3]oxazines and their Applications for the Synthesis of Quinazoline 3‐Oxides
Author(s) -
Lee WenChun,
Shen HoChuan,
Hu WanPing,
Lo WeiSheng,
Murali Chebrolu,
Vandavasi Jaya Kishore,
Wang JehJeng
Publication year - 2012
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.201200018
Subject(s) - chemistry , alkyne , catalysis , oxazines , regioselectivity , stereoselectivity , combinatorial chemistry , aryl , iodine , quinazoline , organic chemistry , alkyl
4‐Benzylidene‐2‐aryl‐4 H ‐benzo[ d ][1,3] oxazines have been synthesized with high stereoselectivity and regioselectivities from 2‐alkynylbenzamides in the presence of a catalytic amount of I 2 . In the reaction mechanism, iodine plays a key role in two different aspects as a catalyst, such as to activate the alkyne with the iodinium donor which triggers the cascade, and then as a proper acid source to facilitate catalyst recovery. The benzoxazines have been exploited as potential substrates for the synthesis of quinazoline 3‐oxide derivatives directly in one step.