ACYLIMIDAZOLIDES AS VERSATILE SYNTHETIC INTERMEDIATES FOR THE PREPARATION OF STERICALLY CONGESTED AMIDES AND KETONES - A PRACTICAL SYNTHESIS OF PROSCAR

被引:7
作者
BHATTACHARYA, A
WILLIAMS, JM
AMATO, JS
DOLLING, UH
GRABOWSKI, EJJ
机构
[1] Merck Sharp & Dohme Research Labaoratories, Process Research Department, 2000 Rahway, N. J.
关键词
D O I
10.1080/00397919008051477
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acylimidazolides react with magnesium amides to produce car-boxamides in excellent yields, whereas Fe(III) catalyzed cross coupling between acylimidazolide and Grignard reagents produce ketones in high yields. These methods were utilized to prepare the a-reductase inhibitor Proscar® as well as various 17β-amide and ketone analogs of Δ1-4-aza-5α-androsten-3-one. © 1990, Taylor & Francis Group, LLC. All rights reserved.
引用
收藏
页码:2683 / 2690
页数:8
相关论文
共 20 条
[1]   SILYLATION-MEDIATED OXIDATION OF 4-AZA-3-KETOSTEROIDS WITH DDQ PROCEEDS VIA DDQ-SUBSTRATE ADDUCTS [J].
BHATTACHARYA, A ;
DIMICHELE, LM ;
DOLLING, UH ;
DOUGLAS, AW ;
GRABOWSKI, EJJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (10) :3318-3319
[2]  
BIRKOFER L, 1975, LIEBIGS ANN CHEM, P2195
[3]   C-ACYLATION UNDER VIRTUALLY NEUTRAL CONDITIONS [J].
BROOKS, DW ;
LU, LDL ;
MASAMUNE, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (01) :72-74
[4]   FUNCTIONALIZED KETONES BY IRON MEDIATED REACTION OF GRIGNARD-REAGENTS WITH ACYL CHLORIDES [J].
CARDELLICCHIO, C ;
FIANDANESE, V ;
MARCHESE, G ;
RONZINI, L .
TETRAHEDRON LETTERS, 1987, 28 (18) :2053-2056
[5]   A CONVENIENT PREPARATION OF BETA-AMINO ALCOHOLS FROM EPOXIDES AND HALOMAGNESIUM ALKYLAMIDES [J].
CARRE, MC ;
HOUMOUNOU, JP ;
CAUBERE, P .
TETRAHEDRON LETTERS, 1985, 26 (26) :3107-3110
[6]  
COSY J, 1989, TETRAHEDRON LETT, V21, P2771
[7]  
KRAFT ME, 1984, J ORG CHEM, V19, P3669
[8]   ALIPHATIC ACID AMIDE GROUPING AS PARTIAL STRUCTURE IN VIRUSTATICS .3. ANTIVIRAL DRUGS [J].
KREUTZBE.A ;
SCHRODER.HH .
ARCHIV DER PHARMAZIE, 1974, 307 (10) :766-774
[9]  
Mestres R., 1982, SYNTHESIS, V288
[10]   SYNTHESIS OF OLEFINS - CROSS COUPLING OF ALKENYL HALIDES AND GRIGNARD-REAGENTS CATALYZED BY IRON COMPLEXES [J].
NEUMANN, SM ;
KOCHI, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (05) :599-606