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
[1]   Tandem [8+2] Cycloaddition-[2+6+2] Dehydrogenation Reactions Involving Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines [J].
Aginagalde, Maialen ;
Vara, Yosu ;
Arrieta, Ana ;
Zangi, Ronen ;
Cebolla, Vicente L. ;
Delgado-Camon, Arantzazu ;
Cossio, Fernando P. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09) :2776-2784
[2]   On the [2+2] cycloaddition of 2-aminothiazoles and dimethyl acetylenedicarboxylate.: Experimental and computational evidence of a thermal disrotatory ring opening of fused cyclobutenes [J].
Alajarin, Mateo ;
Cabrera, Jose ;
Pastor, Aurelia ;
Sanchez-Andrada, Pilar ;
Bautista, Delia .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) :5328-5339
[3]   One pot synthesis using supported reagents system KSCN/SiO2-RNH3OAc/Al2O3:: synthesis of 2-aminothiazoles and N-allylthioureas [J].
Aoyama, T ;
Murata, S ;
Arai, I ;
Araki, N ;
Takido, T ;
Suzuki, Y ;
Kodomari, M .
TETRAHEDRON, 2006, 62 (14) :3201-3213
[4]  
Basarab G., 2008, Appl, Patent No. [WO 2008/152418, 2008152418, WO2008152418 Al]
[5]  
Basarab G. S., 2008, Patent, Patent No. [US2008/132546, 2008132546]
[6]  
Bischler A., 1892, CHEM BER-RECL, V25, P2860, DOI [10.1002/cber.189202502123, DOI 10.1002/CBER.189202502123]
[7]   INVESTIGATION OF THE BISCHLER INDOLE SYNTHESIS FROM 3,5-DIMETHOXYANILINE [J].
BLACK, DSC ;
GATEHOUSE, BMKC ;
THEOBALD, F ;
WONG, LCH .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1980, 33 (02) :343-350
[8]   STABLE BROMONIUM AND IODONIUM IONS OF THE HINDERED OLEFINS ADAMANTYLIDENEADAMANTANE AND BICYCLO[3.3.1]NONYLIDENEBICYCLO[3.3.1]NONANE - X-RAY STRUCTURE, TRANSFER OF POSITIVE HALOGENS TO ACCEPTOR OLEFINS, AND AB-INITIO STUDIES [J].
BROWN, RS ;
NAGORSKI, RW ;
BENNET, AJ ;
MCCLUNG, RED ;
AARTS, GHM ;
KLOBUKOWSKI, M ;
MCDONALD, R ;
SANTARSIERO, BD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) :2448-2456
[9]   1,2,4-TRIAZOL-3-YLPYRIDINES [J].
BROWNE, EJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1975, 28 (11) :2543-2546
[10]   OXIDATION OF OLEFINS WITH SILVER CHROMATE-IODINE - NEW AND FACILE SYNTHESIS OF ALPHA-IODO KETONES [J].
CARDILLO, G ;
SHIMIZU, M .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (26) :4268-4270