A facile and eco-friendly synthesis of diarylthiazoles and diarylimidazoles in water

被引：42

作者：

Kumar, Dalip ^{[1
]}

Kumar, N. Maruthi ^{[1
]}

Patel, Gautam ^{[1
]}

Gupta, Sudeep ^{[1
]}

Varma, Rajender S. ^{[2
]}

机构：

[1] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India

[2] US EPA, Sustainable Technol Div, Natl Risk Management Res Lab, Cincinnati, OH 45268 USA

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 16期

关键词：

Thiazoles; Imidazoles; Greener synthesis; Water; HYPERVALENT IODINE; EXPEDITIOUS SYNTHESIS; CONVENIENT PROCEDURE; ORGANIC-SYNTHESIS; MICHAEL ADDITION; DERIVATIVES; THIAZOLES; CYCLOCONDENSATION; KETONES; AMINOTHIAZOLES;

D O I：

10.1016/j.tetlet.2011.02.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple, efficient and high yielding greener protocol for the synthesis of substituted thiazoles and imidazoles is described that utilizes the reaction of readily available alpha-tosyloxy ketones with variety of thioamides/amidines in water. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1983 / 1986

页数：4

共 57 条

[1] One-pot synthesis of dithiocarbamates accelerated in water [J].

Azizi, N ;

Aryanasab, F ;

Torkiyan, L ;

Ziyaei, A ;

Saidi, MR .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09) :3634-3635

[2] Highly chemoselective addition of amines to epoxides in water [J].

Azizi, N ;

Saidi, MR .

ORGANIC LETTERS, 2005, 7 (17) :3649-3651

[3] A convenient procedure for the solution phase preparation of 2-aminothiazole combinatorial libraries [J].

Bailey, N ;

Dean, AW ;

Judd, DB ;

Middlemiss, D ;

Storer, R ;

Watson, SP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (12) :1409-1414

[4] Parallel synthesis of novel heteroaromatic acromelic acid analogues from kainic acid [J].

Baldwin, JE ;

Fryer, AM ;

Pritchard, GJ .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2588-2596

[5] PHENETHYLTHIAZOLETHIOUREA (PETT) COMPOUNDS, A NEW CLASS OF HIV-1 REVERSE-TRANSCRIPTASE INHIBITORS .1. SYNTHESIS AND BASIC STRUCTURE-ACTIVITY RELATIONSHIP STUDIES OF PETT ANALOGS [J].

BELL, FW ;

CANTRELL, AS ;

HOGBERG, M ;

JASKUNAS, SR ;

JOHANSSON, NG ;

JORDAN, CL ;

KINNICK, MD ;

LIND, P ;

MORIN, JM ;

NOREEN, R ;

OBERG, B ;

PALKOWITZ, JA ;

PARRISH, CA ;

PRANC, P ;

SAHLBERG, C ;

TERNANSKY, RJ ;

VASILEFF, RT ;

VRANG, L ;

WEST, SJ ;

ZHANG, H ;

ZHOU, XX .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (25) :4929-4936

[6]

BENAZZOUZ A, 1995, EUR J PHARMACOL, P284

[7] p38 MAP kinase regulation of oligodendrocyte differentiation with CREB as a potential target [J].

Bhat, Narayan R. ;

Zhang, Peisheng ;

Mohanty, Sangeeta B. .

NEUROCHEMICAL RESEARCH, 2007, 32 (02) :293-302

[8] ON THE ORIGIN OF PRODUCT SELECTIVITY IN AQUEOUS DIELS-ALDER REACTIONS [J].

BRESLOW, R ;

MAITRA, U .

TETRAHEDRON LETTERS, 1984, 25 (12) :1239-1240

[9] SELECTIVE DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTIONS AND SUSPENSIONS [J].

BRESLOW, R ;

MAITRA, U ;

RIDEOUT, D .

TETRAHEDRON LETTERS, 1983, 24 (18) :1901-1904

[10] Water: Nature's Reaction Enforcer-Comparative Effects for Organic Synthesis "In-Water" and "On-Water" [J].

Butler, Richard N. ;

Coyne, Anthony G. .

CHEMICAL REVIEWS, 2010, 110 (10) :6302-6337

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