An efficient solution phase synthesis of triazadibenzoazulenones: 'designer isonitrile free' methodology enabled by microwaves

Christopher Hulme, Shashi Chappeta, Chris Griffith, Yeon Sun Lee, Justin Dietrich

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

A novel two-step solution phase protocol for the synthesis of arrays of triazadibenzoazulenones is reported. The methodology employs the Ugi reaction to assemble desired diversity and acid treatment enables two tandem ring closing transformations. The order of ring closure is shown to be key for optimal conversion to the desired tetra-cyclic product and initially proceeds through a benzimidazole intermediate, followed by second ring closure to give the desired fused benzodiazepine. The two-step protocol is further facilitated by microwave irradiation. Prudent selection of the isonitrile reagent enables the correct order of ring forming events. As such the methodology represents the first example of a post-condensation Ugi modification that employs two internal amino nucleophiles.

Original languageEnglish (US)
Pages (from-to)1939-1942
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number17
DOIs
StatePublished - Apr 29 2009
Externally publishedYes

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Nucleophiles
Microwave irradiation
Microwaves
Benzodiazepines
Condensation
Acids
benzimidazole

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

An efficient solution phase synthesis of triazadibenzoazulenones : 'designer isonitrile free' methodology enabled by microwaves. / Hulme, Christopher; Chappeta, Shashi; Griffith, Chris; Lee, Yeon Sun; Dietrich, Justin.

In: Tetrahedron Letters, Vol. 50, No. 17, 29.04.2009, p. 1939-1942.

Research output: Contribution to journalArticle

Hulme, Christopher ; Chappeta, Shashi ; Griffith, Chris ; Lee, Yeon Sun ; Dietrich, Justin. / An efficient solution phase synthesis of triazadibenzoazulenones : 'designer isonitrile free' methodology enabled by microwaves. In: Tetrahedron Letters. 2009 ; Vol. 50, No. 17. pp. 1939-1942.
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