Practical synthesis of a highly functionalized thiazole ketone

被引:28
作者
Frey, LF [1 ]
Marcantonio, KM [1 ]
Chen, CY [1 ]
Wallace, DJ [1 ]
Murry, JA [1 ]
Tan, LS [1 ]
Chen, WR [1 ]
Dolling, UH [1 ]
Grabowski, EJJ [1 ]
机构
[1] Merck & Co Inc, Dept Proc Res, Merck Res Labs, Rahway, NJ 07065 USA
关键词
thiazole ketone; anion; reaction; difluoromethylation; demethylation;
D O I
10.1016/S0040-4020(03)00878-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Compound 1 is a uniquely substituted ketone prepared via addition of a thiazole anion to an aromatic nitrile in good overall yield. An exploration into the generality of the addition of thiazole anions to nitriles allowed us to make a variety of thiazole ketones in good to excellent yields. The non-odorous thiolate-mediated demethylation reaction used in the synthesis of 1 is also presented. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6363 / 6373
页数:11
相关论文
共 46 条
[1]   O-DEMETHYLATION OF OPIOID DERIVATIVES WITH METHANE SULFONIC-ACID METHIONINE - APPLICATION TO THE SYNTHESIS OF NALOXONE AND ANALOGS [J].
ANDRE, JD ;
DORMOY, JR ;
HEYMES, A .
SYNTHETIC COMMUNICATIONS, 1992, 22 (16) :2313-2327
[2]  
BASTIANELLI P, 1967, B SOC CHIM FR, V6, P1948
[3]  
Battiste M.A., 1987, CHEM CYCLOPROPYL GRO, V1, P255
[4]   Synthesis of new 3-substituted aporphines [J].
Berényi, S ;
Csutorás, C ;
Gyulai, S ;
Rusznyák, G .
SYNTHETIC COMMUNICATIONS, 2001, 31 (13) :1987-1992
[5]  
BIAVA M, 1995, GAZZ CHIM ITAL, V125, P9
[6]   A new synthesis of chloroheterocycles via metal-halogen exchange between trichloroacetyl derivatives and heteroaromatic lithium and Grignard reagents [J].
Boga, C ;
Del Vecchio, E ;
Forlani, L ;
Milanesi, L ;
Todesco, PE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 588 (02) :155-159
[7]   Tetrahalogenomethanes: simple reagents for the synthesis of monohalogenated and mixed dihalogenated aromatic heterocycles via metal-halogen exchange from lithium compounds [J].
Boga, C ;
Del Vecchio, E ;
Forlani, L ;
Todesco, PE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 601 (02) :233-236
[8]  
BRANDSMA L, 1985, SYNTHESIS-STUTTGART, P948
[9]  
CHONG WK, 1998, Patent No. 9921845
[10]  
Christensen S. B., 1996, PCT Int. Appl., Patent No. [WO 9623754, 9623754]