A Van Leusen deprotection-cyclization strategy as a fast entry into two imidazoquinoxaline families

Fabio De Moliner, Christopher Hulme

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

A concise synthesis of two pharmacologically relevant classes of molecules possessing the imidazoquinoxaline core is reported. The protocol involves use of 1,2-phenylenediamines and glyoxylic acid derivatives, namely ethyl glyoxylate or benzylglyoxamide, along with tosylmethylisocyanides in a microwave-assisted Van Leusen three-component condensation. Subsequent unmasking (Boc removal) of an internal amino-nucleophile promotes deprotection and cyclization that take place either spontaneously in a one-pot fashion to give 8 or upon acidic treatment under microwave irradiation after isolation of the imidazole intermediate to give 11. Of note, a tricyclic framework is hence assembled by means of a rapid and straightforward method with a high bond-forming efficiency.

Original languageEnglish (US)
Pages (from-to)5787-5790
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number43
DOIs
StatePublished - Oct 24 2012

Keywords

  • Heterocycles
  • Imidazoquinoxalines
  • Multicomponent reactions
  • TOSMICs

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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