Concise preparation of novel tricyclic chemotypes: Fused hydantoin-benzodiazepines

Steven Gunawan, Gary S. Nichol, Shashi Chappeta, Justin Dietrich, Christopher Hulme

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

The following article describes a concise synthesis of a collection of 4,5-dihydro-1H-benzo[e][1,4]diazepines fused to a hydantoin ring. Molecular complexity and biological relevance are high and structures are generated in a mere three steps, employing the Ugi reaction to assemble diversity reagents. The protocol represents a novel UDC (Ugi-deprotect-cyclize) strategy employed in the Ugi-5-component CO2-mediated condensation, followed by further cyclization under basic conditions, to afford the fused hydantoin. Mechanistic caveats, dependent on the aldehydes of choice will be revealed and a facile oxidation of the final products to imidazolidenetriones is briefly discussed.

Original languageEnglish (US)
Pages (from-to)4689-4692
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number36
DOIs
StatePublished - Sep 8 2010

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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