Iodine-promoted efficient synthesis of diheteroaryl thioethers via the integration of iodination/condensation/cyclization/dehydration sequences

被引：14

作者：

Xue, Wei-Jian ^{[1
]}

Li, Hong-zheng ^{[1
]}

Zheng, Kai-lu ^{[1
]}

Wu, An-xin ^{[1
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 40期

基金：

中国国家自然科学基金;

关键词：

I-2-promoted; Diheteroaryl thioethers; Free of foul-smell thiols; Free of transition metal; Thiourea; ONE-POT SYNTHESIS; CATALYZED CROSS-COUPLINGS; THIA-MICHAEL ADDITION; ARYL HALIDES; ORGANIC SEMICONDUCTORS; MILD CONDITIONS; BOND FORMATION; DIARYL; SULFIDES; THIOLS;

D O I：

10.1016/j.tetlet.2014.08.042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method for the construction of diheteroaryl thioethers from aromatic methyl ketones and thiourea is described. Iodine is the unique catalyst in this protocol. The transformation is free of foul-smell thiols and transition metal. In addition, this method could synthesize two thiazole rings and a sulfur bridge in one pot. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：5544 / 5547

页数：4

共 50 条

[21] Synthesis of (E)-β-iodo vinylsulfones via iodine-promoted iodosulfonylation of alkynes with sodium sulfinates in an aqueous medium at room temperature
Sun, Yadong
Abdukader, Ablimit
Lu, Dong
Zhang, Haiyan
Liu, Chenjiang
[J]. GREEN CHEMISTRY, 2017, 19 (05) : 1255 - 1258
[22] Divergent Synthesis of Benzene Derivatives: Bronsted Acid Catalyzed and Iodine-Promoted Tandem Cyclization of 5,2-Enyn-1-ones
Yang, Fang
Qiu, Yi-Feng
Ji, Ke-Gong
Niu, Yan-Ning
Ali, Shaukat
Liang, Yong-Min
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20): : 9029 - 9037
[23] Iodine-Promoted Oxidative Cyclization of Methyl Azaarenes and α-Amino Ketones for One-Pot Synthesis of 2-Azaaryl-5-aryl Oxazoles
Zhu, Yan-Ping
Zhou, Yu
Li, Wen-Juan
Liu, Fu-Rao
Wang, Wen-Cheng
Hao, Kai-Yan
Chao, Bing-Yu
Shi, Tian-Ru
Wu, An-Xin
Sun, Yuan-Yuan
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (18): : 12460 - 12469
[24] Molecular Iodine-Promoted [3+2] Oxidative Cyclization for the Synthesis of Heteroarene-Fused [1,2,4] Thiadiazoles/Selenadiazoles
Chen, Jin-Yu
Selvaraju, Manikandan
Lin, Yen-Tzu
Dhole, Sandip
Lin, Chih-Yu
Sun, Chung-Ming
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (08): : 5570 - 5579
[25] Iodine-promoted sequential dual oxidative Csp3-H amination/Csp3-H iodination reactions: efficient synthesis of 1-iodoimidazo[1,5-a] pyridines
Wu, Yan-Dong
Geng, Xiao
Gao, Qinghe
Zhang, Jingjing
Wu, Xia
Wu, An-Xin
[J]. ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (11): : 1430 - 1434
[26] Iodine-Promoted Thioylation and Dicarbonylation of Enaminone α-C Sites: Synthesis of Fully Substituted Thiazoles via C=C Bond Cleavage
Zhao, Peng
Zhou, You
Wang, Can
Wu, An-Xin
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (04): : 2505 - 2515
[27] Synthesis of Fully Substituted 5-(o-Hydroxybenzoyl)imidazoles via Iodine-Promoted Domino Reaction of Aurones with Amidines
Xu, Hui
Chen, Hong
Hu, Xiao
Xuan, Guang
Li, Pinhua
Zhang, Ze
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (24): : 16204 - 16212
[28] Iodine-Promoted Metal-Free Cyclization and O/S Exchange ofAcrylamides with Thiuram: One-Step Synthesis of Quinolino-2-thiones
Jiao, Jing
Xiao, Fangtao
Wang, Cheng
Zhang, Zhipeng
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (07): : 4965 - 4970
[29] Iodine-promoted Prins-cyclization of ketones - A facile synthesis of spirocyclic-4-iodotetrahydropyrans and 5,6-dihydro-2H-pyrans
Yadav, J. S.
Reddy, B. V. Subba
Krishna, V. Hari
Swamy, T.
Kumar, G. G. K. S. Narayana
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2007, 85 (06): : 412 - 415
[30] An efficient synthesis of 9-anthrone lactone derivatives via the Knoevenagel condensation and intramolecular cyclization
Tan, Weiqiang
Zheng, Jifang
Guan, Jing
Zhan, Xiuzhi
Gao, Liming
Lyu, Lili
Shan, Bin
Yang, Qipeng
Ma, Mingliang
Xia, Yan
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (03) : 1003 - 1010

← 1 2 3 4 5 →