Facile synthesis of thiazoles via an intramolecular thia-Michael strategy

被引：31

作者：

Sasmal, Pradip K. ^{[1
]}

Sridhar, S. ^{[1
]}

Iqbal, Javed ^{[1
]}

机构：

[1] Dr Reddys Labs Ltd, Discovery Res, Hyderabad 500049, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 49期

关键词：

thiazoles; thia-Michael; benzotriazoles; desilylation;

D O I：

10.1016/j.tetlet.2006.09.157

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient method for the synthesis of substituted thiazoles is reported via one-pot N-desilylation, thioacylation/oxythioacylation/thiothioacylation followed by thia-Michael cycloisomerisation. This method has a general applicability to introduce various oxo and thio functionalities including aliphatic and aromatic moieties, especially at the C2-position of thiazoles. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8661 / 8665

页数：5

共 40 条

[31] Thiopeptide synthesis. alpha-amino thionoacid derivatives of nitrobenzotriazole as thioacylating agents [J].

Shalaby, MA ;

Grote, CW ;

Rapoport, H .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :9045-9048

[32] AN ADDITION-ELIMINATION STRATEGY FOR THE SYNTHESIS OF OXAZOLES [J].

SHORT, KM ;

ZIEGLER, CB .

TETRAHEDRON LETTERS, 1993, 34 (01) :71-74

[33] WS75624-A AND WS75624-B, NEW ENDOTHELIN-CONVERTING ENZYME-INHIBITORS ISOLATED FROM SACCHAROTHRIX SP NO-75624 .1. TAXONOMY, FERMENTATION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITIES [J].

TSURUMI, Y ;

UEDA, H ;

HAYASHI, K ;

TAKASE, S ;

NISHIKAWA, M ;

KIYOTO, S ;

OKUHARA, M .

JOURNAL OF ANTIBIOTICS, 1995, 48 (10) :1066-1072

[34] Solvent-free accelerated organic syntheses using microwaves [J].

Varma, RS .

PURE AND APPLIED CHEMISTRY, 2001, 73 (01) :193-198

[35] REACTIVITY OF IMIDODITHIOCARBONIC ACID .1. CYCLIZATION REACTIONS WITH POTASSIUMALKYLCYANOIMIDODITHIOCARBONATES [J].

WALEK, W ;

PALLAS, M ;

AUGUSTIN, M .

TETRAHEDRON, 1976, 32 (05) :623-627

[36] Synthesis and biological evaluation of novel bisheterocycle-containing compounds as potential anti-influenza virus agents [J].

Wang, WL ;

Yao, DY ;

Gu, M ;

Fan, MZ ;

Li, JY ;

Xing, YC ;

Nan, FJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (23) :5284-5287

[37] A mild and efficient procedure for the synthesis of 1-(alkyldithiocarbonyl)imidazoles [J].

Wang, YQ ;

Ge, ZM ;

Hou, XL ;

Cheng, TM ;

Li, RT .

SYNTHESIS-STUTTGART, 2004, (05) :675-678

[38] One-pot synthesis of thiazoles from pyridazin-3-hydrazidic acid derivatives [J].

Wardakhan, WW ;

Elkholy, YM .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (11) :2661-2673

[39] A practical method for oxazole synthesis by cycloisomerization of propargyl amides [J].

Wipf, P ;

Aoyama, Y ;

Benedum, TE .

ORGANIC LETTERS, 2004, 6 (20) :3593-3595

[40] Total synthesis of dendroamide A: Oxazole and thiazole construction using an oxodiphosphonium salt [J].

You, SL ;

Kelly, JW .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9506-9509

← 1 2 3 4 →