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
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
收藏
页码:1093 / 1101
页数:9
相关论文
共 47 条
  • [11] NOVEL THIAZOLE DERIVATIVES AS INHIBITORS OF SUPEROXIDE PRODUCTION BY HUMAN NEUTROPHILS - SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS
    CHIHIRO, M
    NAGAMOTO, H
    TAKEMURA, I
    KITANO, K
    KOMATSU, H
    SEKIGUCHI, K
    TABUSA, F
    MORI, T
    TOMINAGA, M
    YABUUCHI, Y
    [J]. 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
    DAVE, P
    BYUN, HS
    ENGEL, R
    [J]. SYNTHETIC COMMUNICATIONS, 1986, 16 (11) : 1343 - 1346
  • [14] Unexpected nucleophilic behaviour of free-radicals generated from α-iodoketones
    De Dobbeleer, Corinne
    Pospisil, Jiri
    De Vleeschouwer, Freija
    De Proft, Frank
    Marko, Istvan E.
    [J]. 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
    Donohoe, Timothy J.
    Kabeshov, Mikhail A.
    Rathi, Akshat H.
    Smith, Ian E. D.
    [J]. 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
    FAURE, R
    ASSAF, A
    VINCENT, EJ
    AUNE, JP
    [J]. 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
    Gao, Meng
    Yang, Yan
    Wu, Yan-Dong
    Deng, Cong
    Cao, Li-Ping
    Meng, Xiang-Gao
    Wu, An-Xin
    [J]. 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
    Göblyös, A
    Santiago, SN
    Pietra, D
    Mulder-Krieger, T
    Künzel, JVD
    Brussee, J
    Ijzerman, AP
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (06) : 2079 - 2087