One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines

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

Research output: Contribution to journalArticle

45 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)3732-3735
Number of pages4
JournalOrganic Letters
Volume14
Issue number14
DOIs
StatePublished - Jul 20 2012

Fingerprint

Alkynes
Azides
alkynes
cascades
Quinazolinones
Cycloaddition
Cycloaddition Reaction
cycloaddition
synthesis
aniline
Amides
Iodine
amides
iodine
Condensation
condensation
catalysts
Atoms
Catalysts
Substrates

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines. / Guggenheim, Kathryn G.; Toru, Hannah; Kurth, Mark J.

In: Organic Letters, Vol. 14, No. 14, 20.07.2012, p. 3732-3735.

Research output: Contribution to journalArticle

Guggenheim, Kathryn G. ; Toru, Hannah ; Kurth, Mark J. / One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines. In: Organic Letters. 2012 ; Vol. 14, No. 14. pp. 3732-3735.
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