An economical synthesis of substituted quinoline-2-carboxylates through the potassium persulfate-mediated cross-dehydrogenative coupling of N-aryl glycine derivatives with olefins

被引:32
作者
Liu, Guoliang [3 ]
Qian, Jiarui [1 ]
Hua, Jing [4 ]
Cai, Feng [5 ]
Li, Xia [3 ]
Liu, Lei [1 ,2 ]
机构
[1] Shandong Univ, Sch Pharmaceut Sci, Jinan 250012, Peoples R China
[2] Shandong Univ, Sch Chem & Chem Engn, Educ Minist, Key Lab Colloid & Interface Chem, Jinan 250100, Peoples R China
[3] Shandong Univ, Sch Ocean, Weihai 264209, Peoples R China
[4] Guangxi Normal Univ, Minist Educ China, Key Lab Chem & Mol Engn Med Resources, Guilin 541004, Peoples R China
[5] Shandong Univ, Natl Glycoengn Res Ctr, Jinan 250012, Peoples R China
基金
美国国家科学基金会;
关键词
C-H OXIDATION; TRANSITION-METAL; QUINOLINE-2,4-DICARBOXYLIC ACIDS; STRUCTURALLY DIVERSE; CONVENIENT SYNTHESIS; FUNCTIONALIZATION; ARYLATION; QUINOLINE; BONDS; CONSTRUCTION;
D O I
10.1039/c5ob02216a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and economical K2S2O8-mediated oxidative cross-dehydrogenative coupling of N-aryl glycine derivatives with olefins has been established, affording structurally diverse quinoline-2-carboxylates in good to high efficiency. The low cost, negligible toxicity, and ease of handling of K2S2O8 combined with the absence of hazardous byproducts and the easy workup consisting of simple filtration are attractive based on economic and environmental factors.
引用
收藏
页码:1147 / 1152
页数:6
相关论文
共 73 条
[1]   Intermolecular oxidative cross-coupling of arenes [J].
Ashenhurst, James A. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548
[2]   The interaction of silver nitrate and potassium persulphate and its catalytlic effect in the oxidation of organaic substances. [J].
Austin, PC .
JOURNAL OF THE CHEMICAL SOCIETY, 1911, 99 :262-266
[3]   OXIDATION BY PERSULPHATE .2. OXIDATION EFFECTS WITH A METHYL GROUP AND SOME SUBSTITUTED METHYL GROUPS ON A BENZENE NUCLEUS [J].
BACON, RGR ;
DOGGART, JR .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (MAR) :1332-1338
[4]  
Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109
[5]   A MODIFIED FRIEDLANDER CONDENSATION FOR THE SYNTHESIS OF 3-HYDROXYQUINOLINE-2-CARBOXYLATES [J].
BOGER, DL ;
CHEN, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7369-7371
[6]   Synthesis and in vitro pharmacology of substituted quinoline-2,4-dicarboxylic acids as inhibitors of vesicular glutamate transport [J].
Carrigan, CN ;
Bartlett, RD ;
Esslinger, CS ;
Cybulski, KA ;
Tongcharoensirikul, P ;
Bridges, RJ ;
Thompson, CM .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (11) :2260-2276
[7]   Quinoline-2,4-dicarboxylic acids: Synthesis and evaluation as inhibitors of the glutamate vesicular transport system [J].
Carrigan, CN ;
Esslinger, CS ;
Bartlett, RD ;
Bridges, RJ ;
Thompson, CM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (17) :2607-2612
[8]   Structurally Diverse α-Substituted Benzopyran Synthesis through a Practical Metal-Free C(sp3)-H Functionalization [J].
Chen, Wenfang ;
Xie, Zhiyu ;
Zheng, Hongbo ;
Lou, Hongxiang ;
Liu, Lei .
ORGANIC LETTERS, 2014, 16 (22) :5988-5991
[9]   Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Kwak, Jaesung ;
Chang, Sukbok .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083
[10]  
COREY EJ, 1981, J AM CHEM SOC, V103, P5599, DOI 10.1021/ja00408a067