One-pot reductive cyclization to antitumor quinazoline precursors

Sandip K. Kundu, Mathew P.D. Mahindaratne, Maritza V. Quintero, Ande Bao, George R. Negrete

Research output: Contribution to journalArticle

22 Scopus citations

Abstract

A highly efficient and versatile synthetic approach to the central core of anti-cancer quinazolinone derivatives is reported. Intermolecular reductive N-heterocyclizations of various 2-nitrobenzoic acid derivatives with formamide were catalyzed by indium(III) or bismuth(III) salts to yield the title compounds in high yields and excellent purities. In the present one-pot sequence, the arylnitro group is apparently reduced by formamide decomposition product carbon monoxide and the resultant anthranilic acid derivative proceeds to Niementowski cyclocondensation to form quinazolinones. The transformation is robust for diverse substituents on the aryl group and In(III) counterions, and is also compatible with N-alkyl formamides but not dimethylformamide.

Original languageEnglish (US)
Pages (from-to)33-42
Number of pages10
JournalArkivoc
Volume2008
Issue number2
DOIs
StatePublished - 2008

Keywords

  • Cancer therapeutics
  • Indium(III) acetate
  • Nitro reduction
  • Quinazolinone
  • Reductive heterocyclization

ASJC Scopus subject areas

  • Organic Chemistry

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    Kundu, S. K., Mahindaratne, M. P. D., Quintero, M. V., Bao, A., & Negrete, G. R. (2008). One-pot reductive cyclization to antitumor quinazoline precursors. Arkivoc, 2008(2), 33-42. https://doi.org/10.3998/ark.5550190.0009.205