Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 11-12, Pages 2218-2228Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200018
Keywords
6-exo-dig cyclization; iodine; quinazoline 3-oxides; regioselectivity; stereoselectivity
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Funding
- National Science Council of the Republic of China
- Kaohsiung Medical University Research Foundation
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4-Benzylidene-2-aryl-4H-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.
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