Acyl pyruvates as synthons in the Biginelli reaction

被引：34

作者：

Ryabukhin, Sergey V. ^{[1
,2
]}

Plaskon, Andrey S. ^{[1
,2
]}

Bondarenko, Semen S. ^{[1
]}

Ostapchuk, Eugeniy N. ^{[1
]}

Grygorenko, Oleksandr O. ^{[1
,2
]}

Shishkin, Oleg V. ^{[3
]}

Tolmachev, Andrey A. ^{[1
,2
]}

机构：

[1] Enamine Ltd, UA-01103 Kiev, Ukraine

[2] Kyiv Natl Taras Shevchenko Univ, UA-01033 Kiev, Ukraine

[3] Natl Acad Sci Ukraine, STC Inst Single Crystals, UA-61001 Kharkov, Ukraine

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 32期

关键词：

Multicomponent reactions; Heterocycles; Biginelli reaction; Dihydropyrimidines; Acyl pyruvates; ONE-POT SYNTHESIS; IMPROVED PROTOCOL CONDITIONS; SOLID-PHASE SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; MULTICOMPONENT REACTIONS; COMBINATORIAL LIBRARY; CONDENSATION REACTION; EFFICIENT SYNTHESIS; DOMINO REACTIONS; CHLORIDE;

D O I：

10.1016/j.tetlet.2010.06.032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chlorotrimethylsilane-promoted Biginelli-type reaction of ethyl 2,4-dioxo-4-phenylbutanoate, benzaldehyde, and various (thio)ureas is explored. The outcome of the reaction depends on the structure of the (thio)urea used and is strongly affected by the acceptor electronic properties of the COOEt substituent in the molecule of the starting beta-dicarbonyl compound. The di- and tetrahydropyrimidine derivatives obtained possess two functional groups with orthogonal reactivity, and thus represent promising building blocks for drug discovery. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4229 / 4232

页数：4

共 56 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]

Bannwarth W, 2006, COMBINATORIAL CHEM T

[3]

Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO

[4]

2-A

[5]

Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360

[6]

BONADIES F, 1983, GAZZ CHIM ITAL, V113, P421

[7] 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

[8]

Coudert P, 1996, BIOL PHARM BULL, V19, P220

[9]

Dax SL, 1999, CURR MED CHEM, V6, P255

[10] Ruthenium(III) chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions [J].

De, SK ;

Gibbs, RA .

SYNTHESIS-STUTTGART, 2005, (11) :1748-1750

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