Synthesis of Heterocyclic Aromatic Sulfides under Microwave Irradiation

被引：8

作者：

Zhang, Bianxiang ^{[1
]}

Yang, Lihua ^{[1
]}

Shi, Ruixue ^{[1
]}

Kang, Yongqiang ^{[1
]}

机构：

[1] Shanxi Univ, Sch Chem & Chem Engn, Taiyuan 030006, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 36卷 / 02期

关键词：

2-mercaptobenzo heterocyclic; aryl iodide; aryl thioether; microwave irradiation; high performance liquid chromatography (HPLC); S BOND FORMATION; BIOLOGICAL-ACTIVITIES; COUPLING REACTION; ARYL SULFIDES; DISULFIDES; ARYLATION; THIOLATION; HALIDES; INDOLES;

D O I：

10.6023/cjoc201509026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of the thiolazole compounds with aryl iodide resulted in a series of aryl thioether compounds under microwave irradiation. It showed that the yield of target product was 88% when the reaction was carried out under microwave (30 W) heating for 15 min in N,N-dimethylformamide (DMF). The target products using microwave response and oil bath heating were tracked separately by high performance liquid chromatography (HPLC) analysis under the same conditions. The results showed that the method of microwave irradiation for the preparation of aryl sulfide was simple, efficient, time-saving and less by-products. It is expected to become an efficient, gentle and environmentally friendly synthetic method of heterocyclic aryl sulfides.

引用

页码：352 / 357

页数：6

共 34 条

[1] Copper-catalyzed sulfenylation of pyrroles with disulfides or thiols: directly synthesis of sulfenyl pyrroles [J].

Alves, Diego ;

Lara, Renata G. ;

Contreira, Maria E. ;

Radatz, Catia S. ;

Duarte, Luis F. B. ;

Perin, Gelson .

TETRAHEDRON LETTERS, 2012, 53 (26) :3364-3368

[2]

Azam Mohammed Afzal, 2012, Sci Pharm, V80, P789, DOI 10.3797/scipharm.1204-27

[3] Copper-catalyzed direct thiolation of benzoxazole with diaryl disulfides and aryl thiols [J].

Fukuzawa, Shin-ichi ;

Shimizu, Eiji ;

Atsuumi, Yuka ;

Haga, Masatake ;

Ogata, Kenichi .

TETRAHEDRON LETTERS, 2009, 50 (20) :2374-2376

[4] Design and synthesis of classical and nonclassical 6-arylthio-2,4-diamino-5-ethylpyrrolo[2,3-d]pyrimidines as antifolates [J].

Gangjee, Aleem ;

Zeng, Yibin ;

Talreja, Tina ;

McGuire, John J. ;

Kisliuk, Roy L. ;

Queener, Sherry F. .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (13) :3046-3053

[5] Iodine-catalyzed oxidative system for 3-sulfenylation of indoles with disulfides using DMSO as oxidant under ambient conditions in dimethyl carbonate [J].

Ge, Wenlei ;

Wei, Yunyang .

GREEN CHEMISTRY, 2012, 14 (07) :2066-2070

[6] Substrate-promoted ligand-free CuI catalyzed S-arylation of 2-mercaptobenzothiazoles with aryl iodides in water [J].

He, Guozhen ;

Huang, Yuan ;

Tong, Yao ;

Zhang, Jie ;

Zhao, Dan ;

Zhou, Shuangli ;

Han, Shiqing .

TETRAHEDRON LETTERS, 2013, 54 (39) :5318-5321

[7] Copper-catalyzed direct thiolation of xanthines and related heterocycles with disulfides [J].

He, Zuying ;

Luo, Fang ;

Li, Yinglong ;

Zhu, Gangguo .

TETRAHEDRON LETTERS, 2013, 54 (44) :5907-5910

[8] Microwave-assisted, one-pot syntheses and fungicidal activity of polyfluorinated 2-benzylthiobenzothiazoles [J].

Huang, Wei ;

Yang, Guang-Fu .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (24) :8280-8285

[9] THE REACTIONS OF THIOLS WITH SOME ALKYL AND ARYL HETEROCYCLIC ETHERS [J].

ILLUMINATI, G ;

GILMAN, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (10) :3349-3351

[10] N-heterocyclic carbene copper(I) complex-catalyzed direct C-H thiolation of benzothiazoles [J].

Inomata, Hiroshi ;

Toh, Ayumi ;

Mitsui, Takashi ;

Fukuzawa, Shin-ichi .

TETRAHEDRON LETTERS, 2013, 54 (35) :4729-4731

← 1 2 3 4 →