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 50 条

[21] Bicyclic compounds obtained by the Biginelli reaction
M. M. Kurbanova
Russian Journal of Organic Chemistry, 2010, 46 : 599 - 601
[22] Anticancer Polymers via the Biginelli Reaction
Li, Yongsan
Tan, Tianhao
Zhao, Yuan
Wei, Yen
Wang, Dong
Chen, Rongjun
Tao, Lei
ACS MACRO LETTERS, 2020, 9 (09) : 1249 - 1254
[23] Biginelli Reaction Catalyzed by Copper Nanoparticles
Dewan, Manika
Kumar, Ajeet
Saxena, Amit
De, Arnab
Mozumdar, Subho
PLOS ONE, 2012, 7 (08):
[24] Bicyclic compounds obtained by the Biginelli reaction
Kurbanova, M. M.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (04) : 599 - 601
[25] CuI as reusable catalyst for the Biginelli reaction
Kalita, Hima Rani
Phukan, Prodeep
CATALYSIS COMMUNICATIONS, 2007, 8 (02) : 179 - 182
[26] Modified Biginelli reaction in the synthesis of chromenopyrimidobenzimidazolones
Mazhukina, O. A.
Platonova, A. G.
Fedotova, O. V.
Vasin, V. A.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (05) : 691 - 696
[27] A piperidinium triflate catalyzed Biginelli reaction
Ramalingan, Chennan
Park, Su-Jung
Lee, In-Sook
Kwak, Young-Woo
TETRAHEDRON, 2010, 66 (16) : 2987 - 2994
[28] 2-Phenacylbenzothiazole in the Biginelli reaction
Dzvinchuk, IB
Makitruk, TV
Lozinskii, MO
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2002, (08): : 1141 - 1148
[29] BIGINELLI TYPE REACTION WITH TETROSES DERIVATIVES
FERNANDEZ, MV
HERRERA, FJL
COBOS, TL
HETEROCYCLES, 1988, 27 (09) : 2133 - 2140
[30] Recent progress in asymmetric Biginelli reaction
Heravi, Majid M.
Asadi, Shima
Lashkariani, Boshra Malekzadeh
MOLECULAR DIVERSITY, 2013, 17 (02) : 389 - 407

← 1 2 3 4 5 →