Electrophilic cyclization of 4-thio-but-2-yn-1-ols via 1,2-migration of the thio group: efficient synthesis of 2,4-dihalo-3-thio-substituted furans

被引:14
作者
Zhou, Hongwei [1 ]
Yao, Jinzhong [1 ]
Liu, Guoliang [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
electrophilic cyclization; 1,2-migration of thio group; 2,4-dihalo-3-thio-furan; 4-thio-but-2-yn-1-ol;
D O I
10.1016/j.tetlet.2007.11.092
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and efficient method for the synthesis of 2,4-dihalo-3-thio-furans via the electrophilic cyclization and 1,2-migration of the thio group of 4-thio-but-2-yn-1-ols was developed. As a result of the ready availability of starting materials and the simple and convenient operation, this synthetic route would have potential utility in organic synthesis. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:226 / 228
页数:3
相关论文
共 30 条
[1]   Synthesis of enantiomerically pure 2,2,3,4,5-pentasubstituted pyrrolidines by phenylsulfanyl migration [J].
Baldwin, IC ;
Briner, P ;
Eastgate, MD ;
Fox, DJ ;
Warren, S .
ORGANIC LETTERS, 2002, 4 (25) :4381-4384
[2]   Intramolecular iodoarylation reaction of alkynes:: easy access to derivatives of benzofused heterocycles [J].
Barluenga, J ;
Trincado, M ;
Marco-Arias, M ;
Ballesteros, A ;
Rubio, E ;
González, JM .
CHEMICAL COMMUNICATIONS, 2005, (15) :2008-2010
[3]   Stereoselective substituted pyrrolidine and cyclic ether synthesis by PhS migration [J].
Caggiano, L ;
Davies, J ;
Fox, DJ ;
Moody, DC ;
Warren, S .
CHEMICAL COMMUNICATIONS, 2003, (14) :1648-1649
[4]   Silica gel catalysed generation of episulfonium ions: a mild method for the synthesis of heterocycles [J].
Caggiano, L ;
Fox, DJ ;
Warren, S .
CHEMICAL COMMUNICATIONS, 2002, (21) :2528-2529
[5]  
Fox DJ, 2002, ANGEW CHEM INT EDIT, V41, P2462, DOI 10.1002/1521-3773(20020715)41:14<2462::AID-ANIE2462>3.0.CO
[6]  
2-3
[7]   Isolation of 3H-indole-3,3 bis-sulfides as intermediates in the second sulfenylation of indole [J].
Hamel, P .
TETRAHEDRON LETTERS, 1997, 38 (49) :8473-8474
[8]   Iodine-induced reaction cascades for the rapid construction of variously substituted benzothiophenes [J].
Hessian, KO ;
Flynn, BL .
ORGANIC LETTERS, 2003, 5 (23) :4377-4380
[9]  
HOUSE D, 1999, PHOSPHORUS SULFUR, P153
[10]   1,2-migration of the thio group in allenyl sulfides: Efficient synthesis of 3-thio-substituted furans and pyrroles [J].
Kim, JT ;
Kel'in, AV ;
Gevorgyan, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (01) :98-101