Copper-catalyzed aerobic oxidative amination of sp3 C-H bonds: efficient synthesis of 2-hetarylquinazolin-4(3H)-ones

Qiang Li; Yao Huang; Tieqiao Chen; Yongbo Zhou; Qing Xu; Shuang-Feng Yin; Li-Biao Han

doi:10.1021/ol501454j

Copper-catalyzed aerobic oxidative amination of sp3 C-H bonds: efficient synthesis of 2-hetarylquinazolin-4(3H)-ones

Org Lett. 2014 Jul 18;16(14):3672-5. doi: 10.1021/ol501454j. Epub 2014 Jun 30.

Authors

Qiang Li¹, Yao Huang, Tieqiao Chen, Yongbo Zhou, Qing Xu, Shuang-Feng Yin, Li-Biao Han

Affiliation

¹ State Key Laboratory of Chemo/Biosensing and Chemo metrics, College of Chemistry and Chemical Engineering, Hunan University , Changsha 410082, China.

PMID: 24977337
DOI: 10.1021/ol501454j

Abstract

An efficient synthesis of 2-hetarylquinazolin-4(3H)-ones via copper-catalyzed direct aerobic oxidative amination of sp(3)C-H bonds has been developed. This tandem oxidation-amination-cyclization transformation represents a straightforward protocol to prepare 2-hetaryl-substituted quinazolinones from easily available 2-aminobenzamides and (2-azaaryl)methanes.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amination
Catalysis
Combinatorial Chemistry Techniques
Copper / chemistry*
Cyclization
Heterocyclic Compounds, 3-Ring / chemical synthesis*
Heterocyclic Compounds, 3-Ring / chemistry
Molecular Structure
Oxidation-Reduction
Quinazolinones / chemical synthesis*
Quinazolinones / chemistry

Substances

Heterocyclic Compounds, 3-Ring
Quinazolinones
Copper