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

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.

SUBMITTER: Guggenheim KG

PROVIDER: S-EPMC3486955 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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

Guggenheim Kathryn G KG Toru Hannah H Kurth Mark J MJ

Organic letters 20120629 14

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 mec ...[more]

PMID: 22746550

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