A convenient synthesis of 1,5-diarylpyrazoles from Baylis-Hillman adducts using HY-zeolite

被引：4

作者：

Nikpassand, Mohammad ^{[1
]}

Mamaghani, Manouchehr ^{[1
]}

Zanjanchi, Mohammad Ali ^{[1
]}

Mahmoodi, Nosrat Olah ^{[1
]}

Mirzaeinejad, Massomeh ^{[1
]}

机构：

[1] Univ Guilan, Fac Sci, Dept Chem, Rast 413351914, Iran

来源：

CHINESE CHEMICAL LETTERS | 2010年 / 21卷 / 01期

关键词：

1,5-Diarylpyrazole; HY-zeolite; Baylis-Hillman; Heterogeneous catalysis; CATALYZED N-ARYLATION; ONE-POT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; ACID; HYDRAZONES; ACETATES; LIGANDS; FACILE; AMINES; ESTERS;

D O I：

10.1016/j.cclet.2009.07.020

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile and convenient protocol was developed for the synthesis of 1,5-diarylpyrazoles using Baylis-Hillman adducts in the presence of HY-zeolite as an efficient recyclable heterogeneous catalyst in reasonable reaction times (1.5-2.5 h) and high yields (78-90%). (C) 2009 Manouchehr Mamaghani. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

引用

页码：5 / 8

页数：4

共 29 条

[1] NECIC ACID SYNTHONS .5. TOTAL SYNTHESIS OF (+/-)-RETRONECIC ACID AND RELATED-COMPOUNDS VIA ZINC-MEDIATED COUPLING OF HALOGENO-ESTERS [J].

AMEER, F ;

DREWES, SE ;

HOOLE, R ;

KAYE, PT ;

PITCHFORD, AT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2713-2717

[2] Applications of Baylis-Hillman acetates:: one-pot, facile and convenient synthesis of substituted γ-lactams [J].

Basavaiah, D ;

Rao, JS .

TETRAHEDRON LETTERS, 2004, 45 (08) :1621-1625

[3]

Basavaiah D, 2002, ARKIVOC, P136

[4] A novel Baylis-Hillman protocol for the synthesis of functionalized fused furans [J].

Basavaiah, D ;

Sreenivasulu, B ;

Rao, JS .

TETRAHEDRON LETTERS, 2001, 42 (06) :1147-1149

[5] STEREOCHEMICALLY CONTROLLED SYNTHESIS OF RACEMIC SITOPHILATE, THE AGGREGATIONAL PHEROMONE OF THE GRAIN WEEVIL [J].

CHESKIS, BA ;

MOISEENKOV, AM ;

SHPIRO, NA ;

STASHINA, GA ;

ZHULIN, VM .

BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1990, 39 (04) :716-720

[6] An efficient one-pot synthesis of polyhydroquinolines at room temperature using HY-Zeolite [J].

Das, Biswanath ;

Ravikanth, Bommena ;

Ramu, Ravirala ;

Rao, Bommena Vittal .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (07) :1044-1045

[7] Application of the palladium-catalyzed N-arylation of hydrazones to deactivated heteroaryl halides in the synthesis of pyrazoles [J].

Haddad, N ;

Salvagno, A ;

Busacca, C .

TETRAHEDRON LETTERS, 2004, 45 (30) :5935-5937

[8] Novel application of the palladium-catalyzed N-arylation of hydrazones to a versatile new synthesis of pyrazoles [J].

Haddad, N ;

Baron, J .

TETRAHEDRON LETTERS, 2002, 43 (12) :2171-2173

[9] DABCO-CATALYZED COUPLING OF ALDEHYDES WITH ACTIVATED DOUBLE-BONDS .4. STEREOSELECTIVE SYNTHESIS OF TRISUBSTITUTED OLEFINS AND TERPENOID BUILDING-BLOCKS VIA 2-(HYDROXYALKYL)-2-PROPENOIC ESTERS [J].

HOFFMANN, HMR ;

RABE, J .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3849-3859

[10] Regioselective synthesis of 1,3,5-triaryl-4-alkylpyrazoles: Novel ligands for the estrogen receptor [J].

Huang, YR ;

Katzenellenbogen, JA .

ORGANIC LETTERS, 2000, 2 (18) :2833-2836

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