Citation: Gao Jun, Ren Zhi-Gang, Lang Jian-Ping. One-pot aqueous-phase synthesis of quinoxalines through oxidative cyclization of deoxybenzoins with 1, 2-phenylenediamines catalyzed by a zwtterionic Cu(Ⅱ)/calix[4]arene complex[J]. Chinese Chemical Letters, ;2017, 28(5): 1087-1092. doi: 10.1016/j.cclet.2016.12.035 shu

One-pot aqueous-phase synthesis of quinoxalines through oxidative cyclization of deoxybenzoins with 1, 2-phenylenediamines catalyzed by a zwtterionic Cu(Ⅱ)/calix[4]arene complex

Gao Jun ^a ,
Ren Zhi-Gang ^a,, ,
Lang Jian-Ping ^a,b,,

a.
College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Corresponding author: Ren Zhi-Gang, renzhigang@suda.edu.cn Lang Jian-Ping, jplang@suda.edu.cn
Received Date: 15 November 2016
Revised Date: 12 December 2016
Accepted Date: 15 December 2016
Available Online: 8 May 2017

Figures(5)

A green protocol for the synthesis of quinoxalines has been developed from catalytic oxidative cyclization of deoxybenzoins with 1, 2-phenylenediamines in water. The optimal conditions are involved in the use of a water-soluble mononuclear copper(Ⅱ) complex of a zwitterionic calix[4]arene[Cu(Ⅱ)L(H₂O)]I₂ (1, H₄L=[5, 11, 17, 23-tetrakis (trimethylammonium)-25, 26, 27, 28-tetrahydroxycalix[4]arene]) as a catalyst in alkali solution after refluxing for 15 h in O₂. The target quinoxaline and its derivatives were obtained in good yields (up to 88%). The procedure described in this paper is simple, practical and environmentally benign.
- Aqueous-phase synthesis,
- Quinoxaline,
- Calix[4]arene,
- Cu catalyst,
- Oxidative cyclization
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