Synthesis of 2,3-Disubstituted Quinazolinone Derivatives through Copper Catalyzed C-H Amidation Reactions

Trimurtulu Kotipalli, Veerababurao Kavala, Donala Janreddy, Vijayalakshmi Bandi, Chun Wei Kuo, Ching Fa Yao

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

The synthesis of quinazolinone derivatives was achieved from 2-iodobenzamide derivatives and various benzylamines, allylamine, and cinnamylamine derivatives through a one-pot copper-catalyzed reaction. In this reaction, the amine component (benzylamine/allylamine/cinnamylamine) is N-arylated with 2-iodobenzamide derivatives through Ullman coupling, followed by an intramolecular C-H amidation in the presence of copper catalyst. Copper-catalyzed tandem-Ullman N-alkylation and intramolecular C-H amidation reaction protocol for the synthesis of 2-phenylquinazolinone and quinazolinone derivatives from N-substituted 2-iodo-benzamides and benzylamines, allyl, and cinnamylamine is achieved.

Original languageEnglish
Pages (from-to)1182-1193
Number of pages12
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number6
DOIs
Publication statusPublished - 2016 Feb 1

Keywords

  • Amides
  • Copper
  • Homogeneous catalysis
  • Nitrogen heterocycles
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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