Sodium acetate catalyzed tandem Knoevenagel-Michael multicomponent reaction of aldehydes, 2-pyrazolin-5-ones, and cyano-functionalized C-H acids: Facile and efficient way to 3-(5-hydroxypyrazol-4-yl)-3-aryl-propionitriles

被引:12
作者
Elinson, Michail N. [1 ]
Nasybullin, Ruslan F. [1 ]
Nikishin, Gennady I. [1 ]
机构
[1] ND Zelinskii Inst Organ Chem, Dept Organ Chem, Moscow 119991, Russia
基金
俄罗斯基础研究基金会;
关键词
Aldehydes; Nitrogen heterocycles; Anions; Multicomponent reactions; Michael addition; Synthesis design; MALONONITRILE; CYCLIZATION;
D O I
10.1016/j.crci.2013.03.003
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Sodium acetate catalyzed multicomponent reaction of aryl aldehydes, 2-pyrazolin-5-ones, and malononitrile or alkyl cyanoacetates in alcohols results in the formation of substituted 3-(5-hydroxy-3-methylpyrazol-4-yl)-3-arylpropionitriles in 80-99% yields. The developed efficient catalytic approach to the substituted 3-(5-hydroxy-3-methylpyrazol-4-yl)-3-arylpropionitriles - the promising compounds for human cardiovascular diseases therapy and different biomedical applications - is beneficial from the viewpoint of diversity-oriented large-scale processes and represents facile, efficient and environmentally benign synthetic concept for multicomponent reactions strategy. (C) 2013 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:789 / 794
页数:6
相关论文
共 32 条
[1]   Multicomponent synthesis of 3-heteroarylpropionic acids [J].
Adamo, Mauro F. A. ;
Duffy, Eleanor F. .
ORGANIC LETTERS, 2006, 8 (22) :5157-5159
[2]   Multicomponent synthesis of spiroisoxazolines [J].
Adamo, MFA ;
Donati, D ;
Duffy, EF ;
Sarti-Fantoni, P .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8395-8399
[3]  
Anastas PT, 1998, GREEN CHEMISTRY, P1
[4]  
[Anonymous], 1964, PYRAZOLONES PYRAZOLI
[5]   PYRAZOLONE DERIVATIVES [J].
BROGDEN, RN .
DRUGS, 1986, 32 :60-70
[6]  
Chunguang Y., 2011, ASIAN J CHEM, V23, P749
[7]   Catalyzing the Erlenmeyer Plochl reaction: organic bases versus sodium acetate [J].
Cleary, Thomas ;
Rawalpally, Thimma ;
Kennedy, Nicole ;
Chavez, Flavio .
TETRAHEDRON LETTERS, 2010, 51 (12) :1533-1536
[8]  
Elguero J., 1996, In Comprehensive Heterocyclic Chemistry II, V3
[9]   Facile and convenient synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) by electrocatalytic tandem Knoevenagel-Michael reaction [J].
Elinson, Michail N. ;
Dorofeev, Alexander S. ;
Nasybullin, Ruslan F. ;
Nikishin, Gennady I. .
SYNTHESIS-STUTTGART, 2008, (12) :1933-1937
[10]   Electrocatalytic tandem Knoevenagel-Michael reaction of 3-methyl-2-pyrazolin-5-ones, aryl aldehydes and cyano-functionalized C-H acids: Facile and convenient multicomponent way to substituted 3-(5-hydroxy-3-methylpyrazol-4-yl)-3-arylpropionitriles [J].
Elinson, Michail N. ;
Dorofeev, Alexander S. ;
Nasybullin, Ruslan F. ;
Feducovich, Sergey K. ;
Nikishin, Gennady I. .
ELECTROCHIMICA ACTA, 2008, 53 (15) :5033-5038