Transition Metal Catalyst-Free C-3 Sulfonylmethylation of Imidazo[1,2-a]pyridines with Glyoxylic Acid and Sodium Sulfinates in Water

被引:12
作者
Chen, Jiewen [1 ]
Wen, Kangmei [1 ]
Wu, Yinrong [1 ]
Shi, Jie [1 ]
Yao, Xingang [1 ]
Tang, Xiaodong [1 ]
机构
[1] Southern Med Univ, Sch Pharmaceut Sci, Guangdong Prov Key Lab New Drug Screening, Guangzhou 510515, Peoples R China
关键词
TRIFLUOROMETHYLATION; IMIDAZOHETEROCYCLES; IMIDAZOPYRIDINES; SULFONYLATION; ARYLATION; BROMIDES; ALKENYL; ARYL;
D O I
10.1021/acs.joc.1c02856
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we describe an efficient and benign protocol for direct C-3 sulfonylmethylation of imidazo[1,2-a]pyridines with glyoxylic acid and sodium sulfinates. Various sulfonylmethylated imidazo[1,2-a]pyridines were synthesized in water under transition metal catalyst-free conditions. This multicomponent reaction featured available substrates, good functional group tolerance, moderate to excellent yields, and mild reaction conditions.
引用
收藏
页码:3780 / 3787
页数:8
相关论文
共 36 条
[21]   (Diacetoxy)iodobenzene-Mediated Oxidative C-H Amination of Imidazopyridines at Ambient Temperature [J].
Mondal, Susmita ;
Samanta, Sadhanendu ;
Jana, Sourav ;
Hajra, Alakananda .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (08) :4504-4510
[22]   Regioselective Oxidative Trifluoromethylation of Imidazoheterocycles via C(sp2)-H Bond Functionalization [J].
Monir, Kamarul ;
Bagdi, Avik Kumar ;
Ghosh, Monoranjan ;
Hajra, Alakananda .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03) :1332-1337
[23]   Generation and exploration of new classes of antitubercular agents: The optimization of oxazolines, oxazoles, thiazolines, thiazoles to imidazo[1,2-a]pyridines and isomeric 5,6-fused scaffolds [J].
Moraski, Garrett C. ;
Markley, Lowell D. ;
Chang, Mayland ;
Cho, Sanghyun ;
Franzblau, Scott G. ;
Hwang, Chang Hwa ;
Boshoff, Helena ;
Miller, Marvin J. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (07) :2214-2220
[24]   Trihaloisocyanuric acids in ethanol: an eco-friendly system for the regioselective halogenation of imidazo-heteroarenes [J].
Neto, Jose S. S. ;
Balaguez, Renata A. ;
Franco, Marcelo S. ;
de Sa Machado, Victor C. ;
Saba, Sumbal ;
Rafique, Jamal ;
Galetto, Fabio Z. ;
Braga, Antonio L. .
GREEN CHEMISTRY, 2020, 22 (11) :3410-3415
[25]   Discovery of a novel highly potent broad-spectrum heterocyclic chemical series of arenavirus cell entry inhibitors [J].
Plewe, Michael B. ;
Gantla, Vidyasagar Reddy ;
Sokolova, Nadezda, V ;
Shin, Young-Jun ;
Naik, Shibani ;
Brown, Eric R. ;
Fetsko, Alexandra ;
Zhang, Lihong ;
Kalveram, Birte ;
Freiberg, Alexander N. ;
Henkel, Greg ;
McCormack, Ken .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2021, 41
[26]   Transition-metal-free C-C bond forming reactions of aryl, alkenyl and alkynylboronic acids and their derivatives [J].
Roscales, S. ;
Csaky, A. G. .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (24) :8215-8225
[27]   Transition Metal-Free Synthesis of Carbamates Using CO2 as the Carbon Source [J].
Schilling, Waldemar ;
Das, Shoubhik .
CHEMSUSCHEM, 2020, 13 (23) :6246-6258
[28]   Sodium Salts (NaI/NaBr/NaCl) for the Halogenation of Imidazo-Fused Heterocycles [J].
Semwal, Rashmi ;
Ravi, Chitrakar ;
Kumar, Rahul ;
Meena, Ramavatar ;
Adimurthy, Subbarayappa .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (02) :792-805
[29]  
Tang XD, 2017, ORG BIOMOL CHEM, V15, P8504, DOI [10.1039/c7ob01912brsc.li/obc, 10.1039/c7ob01912b]
[30]   Copper-Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives [J].
Tang, Xiaodong ;
Huang, Liangbin ;
Xu, Yanli ;
Yang, Jidan ;
Wu, Wanqing ;
Jiang, Huanfeng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (16) :4205-4208