One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines

Kathryn G. Guggenheim; Hannah Toru; Mark J. Kurth

doi:10.1021/ol301592z

One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines

Kathryn G. Guggenheim, Hannah Toru, Mark J. Kurth

Chemistry

Research output: Contribution to journal › Article

49 Scopus citations

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.

Original language	English (US)
Pages (from-to)	3732-3735
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	14
DOIs	https://doi.org/10.1021/ol301592z
State	Published - Jul 20 2012

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ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry

Cite this

Guggenheim, K. G., Toru, H., & Kurth, M. J. (2012). One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines. Organic Letters, 14(14), 3732-3735. https://doi.org/10.1021/ol301592z

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Access to Document

10.1021/ol301592z