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Org Lett. 2012 Jul 20;14(14):3732-5. doi: 10.1021/ol301592z. Epub 2012 Jun 29.

One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines.

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1
Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States.

Abstract

An operationally simple, one-pot, two-step cascade method has been developed to afford quinazolino[1,2,3]triazolo[1,4]benzodiazepines. This unique, atom-economical transformation engages five reactive centers (amide, aniline, carbonyl, azide, and alkyne) and employs environmentally benign iodine as a catalyst. The method proceeds via sequential quinazolinone-forming condensation and intramolecular azide-alkyne 1,3-dipolar cycloaddition reactions. Substrate scope, multicomponent examples, and mechanistic insights are discussed.

PMID:
22746550
PMCID:
PMC3486955
DOI:
10.1021/ol301592z
[Indexed for MEDLINE]
Free PMC Article
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