Metal-free direct regioselective thiolation of imidazoheterocycles in water at room temperature

被引:14
作者
Kong, Dulin [1 ,2 ]
Wang, Qinghe [1 ,3 ]
Huang, Tiao [1 ,3 ]
Liang, Min [1 ,3 ]
Lin, Qiang [1 ,3 ]
Wu, Mingshu [1 ,3 ]
机构
[1] Hainan Normal Univ, Coll Chem & Chem Engn, Key Lab Water Pollut Treatment & Resource Reuse H, Haikou 571158, Hainan, Peoples R China
[2] Hainan Med Univ, Sch Pharmaceut Sci, Haikou 571199, Hainan, Peoples R China
[3] Hainan Normal Univ, Coll Chem & Chem Engn, Minist Educ, Key Lab Trop Med Plant Chem, Haikou 571158, Hainan, Peoples R China
关键词
Metal-free; Thiolation; Imidazoheterocycles; Water; C-H; ONE-POT; SULFENYLATION; THIOLS; ENAMINONES; ACCESS;
D O I
10.1016/j.tet.2019.01.059
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free direct thiolation of imidazoheterocycles with various thiophenol in water at room temperature has been developed. In addition, the chemistry provides several advantages including mild condition, high yields, good functional group tolerance, green solvents and suitable for large-scale operations. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1457 / 1463
页数:7
相关论文
共 42 条
[1]   Iodine-catalyzed regioselective thiolation of imidazo[1,2-a]pyridines using sulfonyl hydrazides as a thiol surrogate [J].
Bagdi, Avik Kumar ;
Mitra, Shubhanjan ;
Ghosh, Monoranjan ;
Hajra, Alakananda .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (11) :3314-3320
[2]   N-Fused Imidazoles As Novel Anticancer Agents That Inhibit Catalytic Activity of Topoisomerase IIα and Induce Apoptosis in G1/S Phase [J].
Baviskar, Ashish T. ;
Madaan, Chetna ;
Preet, Ranjan ;
Mohapatra, Purusottam ;
Jain, Vaibhav ;
Agarwal, Amit ;
Guchhait, Sankar K. ;
Kundu, Chanakya N. ;
Banerjee, Uttam C. ;
Bharatam, Prasad V. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (14) :5013-5030
[3]   Metal-free NaI/TBHP-mediated sulfonylation of thiols with sulfonyl hydrazides [J].
Chen, Qian ;
Huang, Yulin ;
Wang, Xiaofeng ;
Wu, Jiawei ;
Yu, Guodian .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (10) :1713-1719
[4]   Direct Condensation of Sulfonamide and Formamide: Nal-Catalyzed Synthesis of N-Sulfonyl Formamidine Using TBHP as Oxidant [J].
Chen, Shulin ;
Xu, Yuan ;
Wan, Xiaobing .
ORGANIC LETTERS, 2011, 13 (23) :6152-6155
[5]  
Chitrakar R., 2017, EUR J ORG CHEM, V2017, P3646
[6]   SYNTHESIS AND ANTIVIRAL ACTIVITY OF 3-SUBSTITUTED IMIDAZO[1,2-A]PYRIDINES [J].
ELHAKMAOUI, A ;
GUEIFFIER, A ;
MILHAVET, JC ;
BLACHE, Y ;
CHAPAT, JP ;
CHAVIGNON, O ;
TEULADE, JC ;
SNOECK, R ;
ANDREI, G ;
DECLERCQ, E .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (16) :1937-1940
[7]   Synthesis of Planar Chiral Ferrocenes via Transition-Metal-Catalyzed Direct C-H Bond Functionalization [J].
Gao, De-Wei ;
Gu, Qing ;
Zheng, Chao ;
You, Shu-Li .
ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (02) :351-365
[8]   Synthesis of imidazo[1,2-a]pyridine C-nucleosides with an unexpected site of ribosylation [J].
Gudmundsson, KS ;
Drach, JC ;
Townsend, LB .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) :3453-3459
[9]   2-amino-3-substituted-6-[(E)-1-phenyl-2-(N-methylcarbamoyl)vinyl]imidazo-[1,2-a]pyridines as a novel class of inhibitors of human rhinovirus:: Stereospecific synthesis and antiviral activity [J].
Hamdouchi, C ;
de Blas, J ;
del Prado, M ;
Gruber, J ;
Heinz, BA ;
Vance, L .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (01) :50-59
[10]   Iodine-catalyzed regioselective sulfenylation of imidazoheterocycles in PEG400 [J].
Hiebel, Marie-Aude ;
Berteina-Raboin, Sabine .
GREEN CHEMISTRY, 2015, 17 (02) :937-944