Three-component one-pot synthetic route to 2-amino-5-alkylidene-thiazol-4-ones

被引：49

作者：

Anderluh, Marko ^{[1
]}

Jukic, Marko ^{[1
]}

Petric, Rok ^{[1
]}

机构：

[1] Univ Ljubljana, Dept Med Chem, Fac Pharm, Ljubljana 1000, Slovenia

来源：

TETRAHEDRON | 2009年 / 65卷 / 01期

关键词：

2-Amino-5-alkylidene-thiazol-4-one; Rhodanine; Knoevenagel condensation; Multi-component reaction; Parallel synthesis; Microwave-assisted organic synthesis; INHIBITORS; DERIVATIVES; GLYCOSYLTRANSFERASE; 4-THIAZOLIDINONES; IDENTIFICATION;

D O I：

10.1016/j.tet.2008.10.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A fast and straightforward three-component reaction to 2-amino-5-alkylidene-thiazol-4-ones is described. The one-pot methodology, reported for the first time, involves Knoevenagel condensation of aromatic aldehydes and rhodanine followed by displacement of the thiocarbonyl sulfur with primary or secondary amines in the same reaction mixture. The reactions were performed using a dedicated microwave reactor, which enabled short reaction times and easy work-up. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：344 / 350

页数：7

共 27 条

[1] 4-thiazolidinones: Novel inhibitors of the bacterial enzyme MurB [J].

Andres, CJ ;

Bronson, JJ ;

D'Andrea, SV ;

Deshpande, MS ;

Falk, PJ ;

Grant-Young, KA ;

Harte, WE ;

Ho, HT ;

Misco, PF ;

Robertson, JG ;

Stock, D ;

Sun, YX ;

Walsh, AW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (08) :715-717

[2] A practical access to novel 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones via sulfur/nitrogen displacement under solvent-free microwave irradiation [J].

Bourahla, Khadidja ;

Derdour, Aicha ;

Rahmouni, Mustapha ;

Carreaux, Francois ;

Bazureau, Jean Pierre .

TETRAHEDRON LETTERS, 2007, 48 (33) :5785-5789

[3]

FRANK R, 2006, Patent No. 2006122777

[4]

Geissman T.A., 1944, Org. React, V2, P94, DOI [DOI 10.1002/0471264180.OR002.03, 10.1002/0471264180.or002.03]

[5]

Hayes B.L., 2002, MICROWAVE SYNTHESIS

[6] Identification of active-site inhibitors of MurG using a generalizable, high-throughput glycosyltransferase screen [J].

Helm, JS ;

Hu, YN ;

Chen, L ;

Gross, B ;

Walker, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11168-11169

[7] Synthesis of heterocycle substituted 1-aryl-4-piperidones [J].

Hu, BH ;

Malamas, M ;

Ellingboe, J .

HETEROCYCLES, 2002, 57 (05) :857-870

[8] New oxadiazolidinedione derivatives as potent and selective human β3 agonists [J].

Hu, BH ;

Malamas, M ;

Ellingboe, J ;

Largis, E ;

Han, S ;

Mulvey, R ;

Tillett, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (08) :981-984

[9] Identification of selective inhibitors for the glycosyltransferase via high-throughput murG screening [J].

Hu, Y ;

Heim, JS ;

Chen, L ;

Ginsberg, C ;

Gross, B ;

Kraybill, B ;

Tiyanont, K ;

Fang, X ;

Wu, T ;

Walker, S .

CHEMISTRY & BIOLOGY, 2004, 11 (05) :703-711

[10] New cyclooxygenase-2/5-lipoxygenase inhibitors.: 3.: 7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran derivatives as gastrointestinal safe antiinflammatory and analgesic agents:: Variations at the 5 position [J].

Janusz, JM ;

Young, PA ;

Ridgeway, JM ;

Scherz, MW ;

Enzweiler, K ;

Wu, LI ;

Gan, LX ;

Chen, J ;

Kellstein, DE ;

Green, SA ;

Tulich, JL ;

Rosario-Jansen, T ;

Magrisso, IJ ;

Wehmeyer, KR ;

Kuhlenbeck, DL ;

Eichhold, TH ;

Dobson, RLM .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (18) :3515-3529

← 1 2 3 →