4.7 Article

Copper-Catalyzed Oxidative Coupling of Quinazoline-3-Oxides:Synthesis of O-Quinazolinic Carbamates

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 8, Pages 5136-5148

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c03098

Keywords

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Funding

  1. National Natural Science Foundation of China [21762025, 21562026]
  2. Key Projects of Natural Science Foundation of Jiangxi Province [20192ACBL200 26]

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Organic carbamates are important structures in both organic chemistry and industry, but the synthesis of hydroxamic acid-based carbamates has received less attention due to the nucleophilicity of both O and N atoms in hydroxamic acids. In this study, a copper-catalyzed oxidative coupling reaction of quinazoline-3-oxides and formamides was reported for the efficient synthesis of O-quinazolinic carbamates. The protocol is practical, and involves simple starting materials and easy operation.
Organic carbamates represent a kind of privileged structures in both organic chemistry and industry. Despite the fact that the synthesis of alcohol-based carbamates has been well studied, an efficient access to hydroxamic acid-based carbamates isless explored due to the nucleophilicity of both O and N atoms inhydroxamic acids. Herein, we report a copper-catalyzed oxidativecoupling of quinazoline-3-oxides and formamides for the synthesis of O-quinazolinic carbamates. This protocol is featured with practicability, simple starting materials, and operational simplicity

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