Facile and convenient synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) by electrocatalytic tandem Knoevenagel-Michael reaction

被引：89

作者：

Elinson, Michail N. ^{[1
]}

Dorofeev, Alexander S. ^{[1
]}

Nasybullin, Ruslan F. ^{[1
]}

Nikishin, Gennady I. ^{[1
]}

机构：

[1] ND Zelinskii Inst Organ Chem, Leninsky Pr 47, Moscow 119991, Russia

来源：

SYNTHESIS-STUTTGART | 2008年 / 12期

关键词：

tandem reactions; electrocatalysis; Knoevenagel reaction; Michael addition; pyrazolone;

D O I：

10.1055/s-2008-1067079

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

An electrochemically induced catalytic tandem Knoevenagel-Michael reaction of two equivalents of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one with various aromatic aldehydes in ethanol in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of the corresponding 4,4'-(arylmethylene)bis(1 H-pyrazol-5-ols) in 80-96% yields. The application of this efficient electrocatalytic method to the synthesis of biologically prominent 4,4'-(arylmethylene)bis(1H-pyrazol-5-ols) represents a facile and convenient approach to the realization of the tandem Knoevenagel-Michael reaction.

引用

页码：1933 / 1937

页数：5

共 39 条

[1]

Ahluwalia VK, 1997, INDIAN J CHEM B, V36, P1059

[2]

3,4-DIPHENYL-1H-PYRAZOLE-1-PROPANAMINE ANTIDEPRESSANTS [J].

BAILEY, DM ;

HANSEN, PE ;

HLAVAC, AG ;

BAIZMAN, ER ;

PEARL, J ;

DEFELICE, AF ;

FEIGENSON, ME .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (02) :256-260

[3]

Behr L. C., 1967, CHEM HETEROCYCLIC CO

[4]

Buzykin B. I., 1971, B ACAD SCI USSR CH, P2224, DOI DOI 10.1007/BF00851295

[5]

Electrochemically induced addition reactions in the absence of solvent and supporting electrolyte [J].

Caruso, Tonino ;

Feroci, Marta ;

Inesi, Achille ;

Orsini, Monica ;

Scettri, Arrigo ;

Palombi, Laura .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (14) :1942-1947

[6]

Tandem and domino catalytic strategies for enantioselective synthesis [J].

Chapman, Christopher J. ;

Frost, Christopher G. .

SYNTHESIS-STUTTGART, 2007, (01) :1-21

[7]

CHAUHAN PMS, 1993, INDIAN J CHEM B, V32, P858

[8]

Recent advances in isocyanide-based multicomponent chemistry [J].

Dömling, A .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2002, 6 (03) :306-313

[9]

Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile:: facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3′-oxindole system [J].

Elinson, Michail N. ;

Ilovaisky, Alexey I. ;

Dorofeev, Alexander S. ;

Merkulova, Valentina M. ;

Stepanov, Nikita O. ;

Miloserdov, Fedor M. ;

Ogibin, Yuri N. ;

Nikishin, Gennady I. .

TETRAHEDRON, 2007, 63 (42) :10543-10548

[10]

The implication of electrocatalysis in MCR strategy:: Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, aldehydes and malononitrile into substituted 5,6,7,8-tetrahydro-4H-chromenes [J].

Elinson, Michail N. ;

Dorofeev, Alexander S. ;

Feducovich, Sergey K. ;

Gorbunov, Sergey V. ;

Nasybullin, Ruslan F. ;

Miloserdov, Fedor M. ;

Nikishin, Gennady I. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (19) :4335-4339

← 1 2 3 4 →