Direct preparation of thiazoles, imidazoles, imidazopyridines and thiazolidines from alkenes

被引：95

作者：

Donohoe, Timothy J. ^{[1
]}

Kabeshov, Mikhail A. ^{[1
]}

Rathi, Akshat H. ^{[1
]}

Smith, Ian E. D. ^{[2
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

[2] GlaxoSmithKline Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 05期

基金：

英国工程与自然科学研究理事会;

关键词：

ONE-POT SYNTHESIS; FACILE SYNTHESIS; ALKYL-HALIDES; OXIDATION; DERIVATIVES; OLEFINS; IODINE; 2-AMINOTHIAZOLES; DEHYDROGENATION; INHIBITORS;

D O I：

10.1039/c1ob06587d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of heterocycles, namely thiazoles, imidazoles, imidazopyridines, thiazolidines and dimethoxyindoles, have been synthesised directly from alkenes via a two-step ketoidoination/cyclisation protocol. The alkene starting materials are themselves readily accessible using many different and well-established approaches, and allow access to a variety of heterocycles with excellent yields and regioselectivity.

引用

页码：1093 / 1101

页数：9

共 47 条

[11] NOVEL THIAZOLE DERIVATIVES AS INHIBITORS OF SUPEROXIDE PRODUCTION BY HUMAN NEUTROPHILS - SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].

CHIHIRO, M ;

NAGAMOTO, H ;

TAKEMURA, I ;

KITANO, K ;

KOMATSU, H ;

SEKIGUCHI, K ;

TABUSA, F ;

MORI, T ;

TOMINAGA, M ;

YABUUCHI, Y .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (02) :353-358

[12]

CORT AD, 1991, J ORG CHEM, V56, P6708

[13] AN IMPROVED DIRECT OXIDATION OF ALKYL-HALIDES TO ALDEHYDES [J].

DAVE, P ;

BYUN, HS ;

ENGEL, R .

SYNTHETIC COMMUNICATIONS, 1986, 16 (11) :1343-1346

[14] Unexpected nucleophilic behaviour of free-radicals generated from α-iodoketones [J].

De Dobbeleer, Corinne ;

Pospisil, Jiri ;

De Vleeschouwer, Freija ;

De Proft, Frank ;

Marko, Istvan E. .

CHEMICAL COMMUNICATIONS, 2009, (16) :2142-2144

[15]

Deprez P., 2006, PROSKELIA SAS, Patent, Patent No. [WO2006/117211, 2006117211]

[16] Direct Preparation of Heteroaromatic Compounds from Alkenes [J].

Donohoe, Timothy J. ;

Kabeshov, Mikhail A. ;

Rathi, Akshat H. ;

Smith, Ian E. D. .

SYNLETT, 2010, (19) :2956-2958

[17]

EVANS RD, 1986, SYNTHESIS-STUTTGART, P727

[18] C-13 NMR-STUDIES OF SUBSTITUTED PHENYLTHIAZOLS - SUBSTITUENT EFFECTS, CONFORMATIONAL-ANALYSIS AND PROTOTROPIC EQUILIBRIUM [J].

FAURE, R ;

ASSAF, A ;

VINCENT, EJ ;

AUNE, JP .

JOURNAL DE CHIMIE PHYSIQUE ET DE PHYSICO-CHIMIE BIOLOGIQUE, 1978, 75 (7-8) :727-734

[19] Formation of Unsymmetrical 1,4-Enediones via A Focusing Domino Strategy: Cross-Coupling of 1,3-Dicarbonyl Compounds and Methyl Ketones or Terminal Aryl Alkenes [J].

Gao, Meng ;

Yang, Yan ;

Wu, Yan-Dong ;

Deng, Cong ;

Cao, Li-Ping ;

Meng, Xiang-Gao ;

Wu, An-Xin .

ORGANIC LETTERS, 2010, 12 (08) :1856-1859

[20] Synthesis and biological evaluation of 2-aminothiazoles and their amide derivatives on human adenosine receptors.: Lack of effect of 2-aminothiazoles as allosteric enhancers [J].

Göblyös, A ;

Santiago, SN ;

Pietra, D ;

Mulder-Krieger, T ;

Künzel, JVD ;

Brussee, J ;

Ijzerman, AP .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (06) :2079-2087

← 1 2 3 4 5 →