Cerium-catalyzed tandem synthesis of 2-substituted benzothiazoles in PEG

被引：17

作者：

Jin, Hui-Le ^{[1
]}

Cheng, Tian-Xing ^{[1
]}

Chen, Jiu-Xi ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2011年 / 25卷 / 03期

基金：

中国国家自然科学基金;

关键词：

benzothiazoles; aldehyde; 2-aminothiophenol; cerium; PEG; SOLVENT-FREE SYNTHESIS; PROMOTED SYNTHESIS; ARYLBORONIC ACIDS; INTRAMOLECULAR CYCLIZATION; ANTITUMOR BENZOTHIAZOLES; MICROWAVE IRRADIATION; POLY(ETHYLENE GLYCOL); POLYETHYLENE-GLYCOL; 2-ARYLBENZOTHIAZOLES; ALDEHYDES;

D O I：

10.1002/aoc.1750

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient and convenient condensation reaction of 2-aminothiophenol with aldehydes catalyzed by a catalytic amount of ceric ammonium nitrate in polyethylene glycol was investigated. As a result, a set of diverse 2-substituted benzothiazoles such as 2-phenylbenzothiazole as well as its p-Me, p-NO(2), p-F, p-Cl, p-Br, o-OMe, p-OMe and 2-furyl, 2-pyridyl and styryl derivatives were obtained in good to excellent yields for 5 h at room temperature. Additionally, the catalyst system was recovered and reused several times without evident loss in activity. Copyright (C) 2011 John Wiley & Sons, Ltd.

引用

页码：238 / 240

页数：3

共 42 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]

AZARIFAR D, 2009, RELAT ELEM, V184, P2097

[3] Synthesis of 2-substituted-benzothiazoles by palladium-catalyzed intramolecular cyclization of o-bromophenylthioureas and o-bromophenylthioamides [J].

Benedí, C ;

Bravo, F ;

Uriz, P ;

Fernández, E ;

Claver, C ;

Castillón, S .

TETRAHEDRON LETTERS, 2003, 44 (32) :6073-6077

[4] CONVENIENT PREPARATION OF 2-SUBSTITUTED BENZOTHIAZOLES [J].

BOGER, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (11) :2296-2297

[5] 2-(4-aminophenyl)benzothiazoles: novel agents with selective profiles of in vitro anti-tumour activity [J].

Bradshaw, TD ;

Wrigley, S ;

Shi, DF ;

Schultz, RJ ;

Paull, KD ;

Stevens, MFG .

BRITISH JOURNAL OF CANCER, 1998, 77 (05) :745-752

[6] Osmium tetroxide in poly(ethylene glycol) (PEG): a recyclable reaction medium for rapid asymmetric dihydroxylation under Sharpless conditions [J].

Chandrasekhar, S ;

Narsihmulu, C ;

Sultana, SS ;

Reddy, NR .

CHEMICAL COMMUNICATIONS, 2003, (14) :1716-1717

[7] Polyethylene glycol and solutions of polyethylene glycol as green reaction media [J].

Chen, J ;

Spear, SK ;

Huddleston, JG ;

Rogers, RD .

GREEN CHEMISTRY, 2005, 7 (02) :64-82

[8] Gallium(III) triflate-catalyzed one-pot selective synthesis of 2 3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones [J].

Chen, Jiuxi ;

Wu, Dengze ;

He, Fei ;

Liu, Miaochang ;

Wu, Huayue ;

Ding, Jinchang ;

Su, Weike .

TETRAHEDRON LETTERS, 2008, 49 (23) :3814-3818

[9] An approach to the Paal-Knorr pyrroles synthesis catalyzed by Sc(OTf)3 under solvent-free conditions [J].

Chen, Jiuxi ;

Wu, Huayue ;

Zheng, Zhiguo ;

Jin, Can ;

Zhang, Xingxian ;

Su, Weike .

TETRAHEDRON LETTERS, 2006, 47 (30) :5383-5387

[10] Solvent-free synthesis of β-hydroxy esters and β-amino esters by indium-mediated reformatsky reaction [J].

Chen, Xi'an ;

Zhang, Changfu ;

Wu, Huayue ;

Yu, Xiaochun ;

Su, Weike ;

Cheng, Jiang .

SYNTHESIS-STUTTGART, 2007, (20) :3233-3239

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