A highly regioselective synthesis of 2-aryl-6-chlorobenzothiazoles employing microwave-promoted Suzuki-Miyaura coupling reaction

被引：63

作者：

Heo, Y ^{[1
]}

Song, YS ^{[1
]}

Kim, BT ^{[1
]}

Heo, JN ^{[1
]}

机构：

[1] Korea Res Inst Chem Technol, Bioorgan Sci Div, Taejon 305600, South Korea

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 18期

关键词：

Suzuki-Miyaura reaction; palladium; boronic acid; microwave; benzothiazole; amination;

D O I：

10.1016/j.tetlet.2006.02.152

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Suzuki-Miyaura coupling reactions of 2,6-dichlorobenzothiazole with arylboronic acids, promoted by microwave heating, efficiently produce 2-aryl-6-chlorobenzothiazoles in a highly regioselective manner. This process serves as the foundation for a simple method to rapidly construct 2-aryl-6-chlorobenzothiazole libraries. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3091 / 3094

页数：4

共 37 条

[1] One-step synthesis of 2-arylbenzothiazole ('BTA') and -benzoxazole precursors for in vivo imaging of β-amyloid plaques [J].

Alagille, D ;

Baldwin, RM ;

Tamagnan, GD .

TETRAHEDRON LETTERS, 2005, 46 (08) :1349-1351

[2] General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].

Anderson, KW ;

Buchwald, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177

[3]

Appukkuttan P, 2003, SYNLETT, P1204

[4] SYNTHESIS OF 2-SUBSTITUTED BENZOTHIAZOLES FROM 2-FLUOROPHENYLISOTHIOCYANATE [J].

ARES, JJ .

SYNTHETIC COMMUNICATIONS, 1991, 21 (05) :625-633

[5] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[6] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].

Bellina, F ;

Carpita, A ;

Rossi, R .

SYNTHESIS-STUTTGART, 2004, (15) :2419-2440

[7] Novel synthesis of 2-arylbenzothiazoles - Microwave-activated electron transfer [J].

BenAlloum, A ;

Bakkas, S ;

Soufiaoui, M .

TETRAHEDRON LETTERS, 1997, 38 (36) :6395-6396

[8] Microwave-assisted aqueous Suzuki cross-coupling reactions [J].

Blettner, CG ;

König, WA ;

Stenzel, W ;

Schotten, T .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3885-3890

[9] An efficient synthesis of benzothiazoles by direct condensation of carboxylic acids with 2-aminothiophenol under microwave irradiation [J].

Chakraborti, AK ;

Selvam, C ;

Kaur, G ;

Bhagat, S .

SYNLETT, 2004, (05) :851-855

[10] Efficient Pd-catalyzed amination of heteroaryl halides [J].

Charles, MD ;

Schultz, P ;

Buchwald, SL .

ORGANIC LETTERS, 2005, 7 (18) :3965-3968

← 1 2 3 4 →