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Synthesis 2011(3): 387-396  
DOI: 10.1055/s-0030-1258375
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© Georg Thieme Verlag Stuttgart ˙ New York

DABCO-Catalyzed Oxidation of Deoxybenzoins to Benzils with Air and One-Pot Synthesis of Quinoxalines

Chaorong Qi, Huanfeng Jiang*, Liangbin Huang, Zhengwang Chen, Huoji Chen
School of Chemistry and Chemical Engineering, South China University of Technology, 381 Wushan Road, Guangzhou 510640, P. R. of China
Fax: +86(20)87112906; e-Mail: jianghf@scut.edu.cn;
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Publication History

Received 27 September 2010
Publication Date:
17 December 2010 (online)

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Abstract

Aerobic oxidation of deoxybenzoins could be efficiently catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) with air as the sole oxidant to give the corresponding benzils in excellent yields. The effects of reaction conditions, such as different bases, temperature, time and solvent, on the yield of the product were investigated. Moreover, the process has been successfully extended to a one-pot synthesis of quinoxalines from benzyl ketones and aromatic 1,2-diamines.

Key words

deoxybenzoins - benzils - oxidation - quinoxalines - 1,2-diamines