| 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 |
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| 作者姓名： | Jun Gao Zhi-Gang Ren Jian-Ping Lang |
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| 作者单位： | 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 |
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| 摘 要： | 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 calix4]areneCu(Ⅱ)LCH_2O)]I_2(1,H_4L=5,ll,17,23-tetrakis(trimethylammonium)-25,26,27,28-tetrahydroxycalix4]arene]) as a catalyst in alkali solution after refluxing for 15 h in O_2.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.
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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 |
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| Jun Gao,Zhi-Gang Ren,Jian-Ping Lang.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. |
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| Authors: | Jun Gao Zhi-Gang Ren Jian-Ping Lang |
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| Institution: | 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 |
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| Abstract: | 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 calix4]areneCu(II)L(H2O)]I2 (1, H4L=5,11,17,23-tetrakis (trimethylammonium)-25,26,27,28-tetrahydroxycalix4]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. |
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| Keywords: | Aqueous-phase synthesis Quinoxaline Calix[4]arene Cu catalyst Oxidative cyclization |
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