Catalyst-Free One-Pot Multi-Component Synthesis of 2-Substituted Quinazolin-4-carboxamides from 2-Aminophenyl-2-oxoacetamides, Aldehydes, and Ammonium Acetate

Seung Hwan Shim, Hyejun Park, Neeraj Kumar Mishra, In Su Kim, Jae Kyun Lee, Kiho Lee, Hitesh B. Jalani, Yongseok Choi

Research output: Contribution to journalArticlepeer-review

Abstract

Herein, we report a simple and straightforward catalyst-free one-pot multi-component synthesis of quinazolin-4-carboxamides using 2-(2-aminophenyl)-N,N-dialkyl-2-oxoacetamide, aldehydes and ammonium acetate. As compared to the conventional approached for quinazolin-4-carboxamides synthesis, this transformation demonstrates very good reactivity by tolerating a large number of functional groups, and proceeds with good to moderate yields under mild conditions. Notably, the synthesized 6-bromoquinazolin-4-carboxamide was subjected to Suzuki-Miyaura cross-coupling and Buchwald-Hartwig C−N bond forming reactions providing a straightforward method to obtain structurally diverse and valuable quinazoline scaffolds. Furthermore, the reaction could be easily scaled up to gram scale.

Original languageEnglish
Pages (from-to)5446-5450
Number of pages5
JournalChemistrySelect
Volume6
Issue number22
DOIs
Publication statusPublished - 2021 Jun 15

Keywords

  • Carboxamide
  • Catalyst-Free
  • Multicomponent Reaction
  • N-Heterocycles
  • One-Pot Synthesis
  • Quinazoline

ASJC Scopus subject areas

  • Chemistry(all)

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