A FACILE ROUTE TO IMIDAZOL-4-YL ANIONS AND THEIR REACTION WITH CARBONYL-COMPOUNDS

被引:73
作者
TURNER, RM
LINDELL, SD
LEY, SV
机构
[1] SCHERING AGROCHEM LTD,CHESTERFORD PK RES STN,WALDEN CB10 1XL,ESSEX,ENGLAND
[2] IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND
关键词
D O I
10.1021/jo00020a002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of N-protected 4-iodoimidazoles 1-3 in CH2Cl2 solution with an ethereal solution of ethyl-magnesium bromide generates the corresponding imidazol-4-yl anions, which react with carbonyl compounds to give carbinols 4-14 in 60-83% yield.
引用
收藏
页码:5739 / 5740
页数:2
相关论文
共 31 条
[1]   STUDIES OF ACTIVATED COMPOUND .3. SYNTHESIS OF MUSCALURE - (ZETA)-9-TRICOSENE [J].
ABE, K ;
YAMASAKI, T ;
NAKAMURA, N ;
SAKAN, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (10) :2792-2792
[2]  
BABUDRI F, 1985, SYNTHESIS-STUTTGART, P522
[3]  
BUSS AD, 1988, Patent No. 284277
[4]   HIGH-YIELDING SYNTHESES OF 4(5)-SUBSTITUTED IMIDAZOLES VIA ORGANOLITHIUM INTERMEDIATES - THE UTILITY OF SULFONAMIDE N-PROTECTION AND SILICON-CONTAINING BLOCKING GROUPS [J].
CARPENTER, AJ ;
CHADWICK, DJ .
TETRAHEDRON, 1986, 42 (08) :2351-2358
[5]   MONOALKYLAMINOMETHYLATION OF ORGANOMETALLIC COMPOUNDS USING N-ALKYL-N-TRIMETHYLSILYL ALKOXYMETHYLAMINES [J].
COURTOIS, G ;
MIGINIAC, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 340 (02) :127-141
[6]   REASSIGNMENT OF THE STRUCTURES OF IODONITROIMIDAZOLE, ITS N-METHYL DERIVATIVES, AND RELATED-COMPOUNDS [J].
DICKENS, JP ;
DYER, RL ;
HAMILL, BJ ;
HARROW, TA ;
BIBLE, RH ;
FINNEGAN, PM ;
HENRICK, K ;
OWSTON, PG .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (09) :1781-1786
[7]  
DUDFIELD PJ, 1990, SYNLETT, P277
[8]   CYANOGUANIDINE-THIOUREA EQUIVALENCE IN DEVELOPMENT OF HISTAMINE H-2-RECEPTOR ANTAGONIST, CIMETIDINE [J].
DURANT, GJ ;
EMMETT, JC ;
GANELLIN, CR ;
MILES, PD ;
PARSONS, ME ;
PRAIN, HD ;
WHITE, GR .
JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (07) :901-906
[9]  
ELBORAI M, 1981, CROAT CHEM ACTA, V54, P211
[10]   SIMPLE AND CHEMOSELECTIVE SYNTHESIS OF KETONES FROM CARBOXYLIC-ACIDS AND GRIGNARD-REAGENTS USING DICHLOROTRIPHENYLPHOSPHORANE [J].
FUJISAWA, T ;
IIDA, S ;
UEHARA, H ;
SATO, T .
CHEMISTRY LETTERS, 1983, (08) :1267-1270