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

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 t...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 3; pp. 387 - 396
Main Authors Qi, Chaorong, Jiang, Huanfeng, Huang, Liangbin, Chen, Zhengwang, Chen, Huoji
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.02.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
deoxybenzoins
ROOM-TEMPERATURE
benzils
ALPHA-HYDROXY KETONES
TANDEM OXIDATION
WEAK CARBON ACIDS
O-PHENYLENEDIAMINES
oxidation
1,2-diamines
LIGHT-EMITTING-DIODES
BIOLOGICAL-ACTIVITY
SINGLET OXYGEN
EFFICIENT
quinoxalines
MOLECULAR-OXYGEN
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Summary: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.
ISSN:0039-7881
DOI:10.1055/s-0030-1258375