4.4 Article

Bismuth-catalyzed synthesis of 2-substituted quinazolinones

Journal

TETRAHEDRON LETTERS
Volume 59, Issue 42, Pages 3801-3805

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2018.09.014

Keywords

Bismuth; Catalysis; Quinazolinone; Green chemistry; Condensation

Funding

  1. North Dakota State University
  2. NIH NIGMS [P30 GM103332]
  3. National Science Foundation [IIA-1355466]

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The bismuth-catalyzed oxidative condensation of aldehydes with 2-aminobenzamide under aerobic conditions is reported using ethanol as the solvent. Good to excellent isolated yields (68-95%) of the corresponding 2-substituted quinazolinones were obtained under mild reaction conditions with excellent functional group tolerance. The quinazolinones were further functionalized to afford N-allylated quinazolinones, 2-aminopyridine derivatives, and annulated polyheterocyclic compounds via transition-metal catalyzed reactions. (C) 2018 Elsevier Ltd. All rights reserved.

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