MCC/SNAr methodology. Part 1: Novel access to a range of heterocyclic cores

Paul Tempest, Vu Ma, Michael G. Kelly, Wyeth Jones, Christopher Hulme

Research output: Contribution to journalArticle

80 Citations (Scopus)

Abstract

The novel solution-phase syntheses of arrays of biologically relevant indazolinones, benzazepines and benzoxazepines, utilizing multi-component condensation (MCC)/SNAr methodology is reported. Reaction of commercially available 2-fluoro-5-nitrobenzoic acid with an aldehyde, isonitrile and a primary amine tethered to a Boc-protected internal amino or hydroxyl nucleophile, affords the Ugi product in good yield. Subsequent acid treatment followed by proton scavenging promotes cyclization of internal amino nucleophiles to a variety of ring sizes. Base treatment alone is sufficient to generate benzoxazepines. Interestingly, this communication also introduces a highly efficient two-step route to benzimidazoles.

Original languageEnglish (US)
Pages (from-to)4963-4968
Number of pages6
JournalTetrahedron Letters
Volume42
Issue number30
DOIs
StatePublished - Jul 23 2001
Externally publishedYes

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Benzazepines
Nitrobenzoates
Benzimidazoles
Nucleophiles
Cyclization
Aldehydes
Hydroxyl Radical
Amines
Protons
Condensation
Acids
Scavenging
Communication

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

MCC/SNAr methodology. Part 1 : Novel access to a range of heterocyclic cores. / Tempest, Paul; Ma, Vu; Kelly, Michael G.; Jones, Wyeth; Hulme, Christopher.

In: Tetrahedron Letters, Vol. 42, No. 30, 23.07.2001, p. 4963-4968.

Research output: Contribution to journalArticle

Tempest, Paul ; Ma, Vu ; Kelly, Michael G. ; Jones, Wyeth ; Hulme, Christopher. / MCC/SNAr methodology. Part 1 : Novel access to a range of heterocyclic cores. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 30. pp. 4963-4968.
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