The preparation and Wittig condensations of C-4 thiazole phosphonium methylides

被引:18
作者
Williams, DR [1 ]
Brooks, DA [1 ]
Moore, JL [1 ]
Stewart, AO [1 ]
机构
[1] ABBOTT LABS,ABBOTT PK,IL 60064
基金
美国国家卫生研究院;
关键词
thiazole synthesis; phosphonium salts;
D O I
10.1016/0040-4039(95)02358-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A modification of the Hantzsch thiazole synthesis is described which produces C-4 thiazolylmethyl phosphonium salts. Ylides are condensed with a variety of aldehydes to produce a series of 2,4-disubstituted thiazoles.
引用
收藏
页码:983 / 986
页数:4
相关论文
共 29 条
[1]   REINVESTIGATION OF A MODIFIED HANTZSCH THIAZOLE SYNTHESIS [J].
AGUILAR, E ;
MEYERS, AI .
TETRAHEDRON LETTERS, 1994, 35 (16) :2473-2476
[2]   STRUCTURE OF CYCLOTHIAZOMYCIN, A UNIQUE POLYTHIAZOLE-CONTAINING PEPTIDE WITH RENIN INHIBITORY ACTIVITY .2. TOTAL STRUCTURE [J].
AOKI, M ;
OHTSUKA, T ;
ITEZONO, Y ;
YOKOSE, K ;
FURIHATA, K ;
SETO, H .
TETRAHEDRON LETTERS, 1991, 32 (02) :221-224
[3]   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
[4]   MYCOTHIAZOLE, A POLYKETIDE HETEROCYCLE FROM A MARINE SPONGE [J].
CREWS, P ;
KAKOU, Y ;
QUINOA, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) :4365-4368
[5]   THIAZOLYLMETHYLENETRIPHENYLPHOSPORANE AND ITS BENZO DERIVATIVE - STABLE AND PRACTICAL WITTIG REAGENTS FOR THE SYNTHESIS OF VINYLTHIAZOLES AND VINYLBENZOTHIAZOLES - 2-CARBON HOMOLOGATION OF ALDEHYDES [J].
DONDONI, A ;
FANTIN, G ;
FOGAGNOLO, M ;
MEDICI, A ;
PEDRINI, P .
TETRAHEDRON, 1988, 44 (07) :2021-2031
[6]   TOTAL SYNTHESIS OF (+)-GALACTOSTATIN - AN ILLUSTRATION OF THE UTILITY OF THE THIAZOLE-ALDEHYDE SYNTHESIS [J].
DONDONI, A ;
PERRONE, D .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4749-4754
[7]  
HAMADA Y, 1992, J ORG CHEM, V57, P6671
[8]  
HARA M, 1989, J ANTIBIOT, V42, P1768
[9]   STRUCTURAL BIOCHEMISTRY .23. SYNTHESIS OF THE DOLASTATIN THIAZOLE AMINO-ACID COMPONENT (GLN)THZ [J].
HOLZAPFEL, CW ;
PETTIT, GR .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2323-2327
[10]   PREPARATION OF CHLOROMETHYL VINYL KETONES [J].
HUDSON, RF ;
CHOPARD, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (09) :2446-&