Cyclic ketones and substituted α-keto acids as alternative substrates for novel Biginelli-like scaffold syntheses

被引:89
作者
Abelman, MM
Smith, SC
James, DR
机构
[1] Signature BioSci Inc, Richmond, CA 94804 USA
[2] Syngenta Ltd, Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England
关键词
Biginelli; alpha-keto acid; dihydropyrimidinone; pyrrolidinium tosylate;
D O I
10.1016/S0040-4039(03)00985-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reactions of benzocyclic ketones and alpha-ketoacids as carbonyl components in the Biginelli reaction were investigated. These unusual Biginelli substrates furnished novel drug-like dihydropyrimidinone scaffolds suitable for further elaboration. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4559 / 4562
页数:4
相关论文
共 15 条
[1]   Multiple-component condensation strategies for combinatorial library synthesis [J].
Armstrong, RW ;
Combs, AP ;
Tempest, PA ;
Brown, SD ;
Keating, TA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131
[2]   In vitro and in vivo evaluation of dihydropyrimidinone C-5 amides as potent and selective α1A receptor antagonists for the treatment of benign prostatic hyperplasia [J].
Barrow, JC ;
Nantermet, PG ;
Selnick, HG ;
Glass, KL ;
Rittle, KE ;
Gilbert, KF ;
Steele, TG ;
Homnick, CF ;
Freidinger, RM ;
Ransom, RW ;
Kling, P ;
Reiss, D ;
Broten, TP ;
Schorn, TW ;
Chang, RSL ;
O'Malley, SS ;
Olah, TV ;
Ellis, JD ;
Barrish, A ;
Kassahun, K ;
Leppert, P ;
Nagarathnam, D ;
Forray, C .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (14) :2703-2718
[3]   A new substrate for the Biginelli cyclocondensation:: Direct preparation of 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones from a β-keto carboxylic acid [J].
Bussolari, JC ;
McDonnell, PA .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6777-6779
[4]   New regioselective multicomponent reaction: One pot synthesis of spiro heterobicyclic aliphatic rings [J].
Byk, G ;
Gottlieb, HE ;
Herscovici, J ;
Mirkin, F .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (06) :732-735
[5]  
Dömling A, 1998, COMB CHEM HIGH T SCR, V1, P1
[6]  
Falsone F. S., 2001, ARKIVOC, P122
[7]   Unprecedented catalytic three component one-pot condensation reaction: An efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones [J].
Hu, EH ;
Sidler, DR ;
Dolling, UH .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3454-3457
[8]   p-toluenesulfonic acid-catalyzed efficient synthesis of dihydropyrimidines:: Improved high yielding protocol for the Biginelli reaction [J].
Jin, TS ;
Zhang, SL ;
Li, TS .
SYNTHETIC COMMUNICATIONS, 2002, 32 (12) :1847-1851
[9]   4-aryldihydropyrimidines via the Biginelli condensation: Aza-analogs of nifedipine-type calcium channel modulators [J].
Kappe, CO .
MOLECULES, 1998, 3 (01) :1-9
[10]  
KAPPE CO, 1993, TETRAHEDRON, V49, P6937