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

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 24期

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

页码：4559 / 4562

页数：4

共 15 条

[1] Multiple-component condensation strategies for combinatorial library synthesis
Armstrong, RW
Combs, AP
Tempest, PA
Brown, SD
Keating, TA
[J]. 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
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
[J]. 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
Bussolari, JC
McDonnell, PA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) : 6777 - 6779
[4] New regioselective multicomponent reaction: One pot synthesis of spiro heterobicyclic aliphatic rings
Byk, G
Gottlieb, HE
Herscovici, J
Mirkin, F
[J]. 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
Hu, EH
Sidler, DR
Dolling, UH
[J]. 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
Jin, TS
Zhang, SL
Li, TS
[J]. SYNTHETIC COMMUNICATIONS, 2002, 32 (12) : 1847 - 1851
[9] 4-aryldihydropyrimidines via the Biginelli condensation: Aza-analogs of nifedipine-type calcium channel modulators
Kappe, CO
[J]. MOLECULES, 1998, 3 (01) : 1 - 9
[10] KAPPE CO, 1993, TETRAHEDRON, V49, P6937

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