New Convenient Four-Component Synthesis of 6-Amino-2,4-dihydropyrano[2,3-c]pyrazol-5-carbonitriles and One-Pot Synthesis of 6′-Aminospiro[(3H)-indol-3,4′-pyrano[2,3-c]pyrazol]-(1H)-2-on-5′-carbonitriles

被引：124

作者：

Litvinov, Yuri M. ^{[1
]}

Shestopalov, Alexander A. ^{[1
]}

Rodinovskaya, Lyudmila A. ^{[1
]}

Shestopalov, Anatoliy M. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2009年 / 11卷 / 05期

基金：

俄罗斯基础研究基金会;

关键词：

MULTICOMPONENT REACTIONS; COMBINATORIAL SYNTHESIS; HETEROCYCLIC-COMPOUNDS; MOLLUSCICIDAL ACTIVITY; CARBONYL-COMPOUNDS; CYANOACETIC ACID; DERIVATIVES; 1,4-DIHYDROPYRIDINES; 6-AMINO-5-CYANO-2-METHYL-4-(1-NAPHTHYL)-4H-PYRAN-3-CARBOXYLATE; PYRANOPYRAZOLES;

D O I：

10.1021/cc900076j

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

This report describes a new four-component synthesis of substituted and spiro-conjugated 6-amino-2H,4H-pyrano[2,3-c] pyrazol-5-carbonitriles directly from aromatic aldehydes or heterocyclic ketones, malononitrile, beta-ketoesters, and hydrazine hydrate. The method provides a convenient one-pot route toward divers 2,4-dihydropyrano[2,3-c]pyrazoles, whereas a modified one-step sequential protocol gives access to spiro[indoline-3,4'-pyrano[2,3-c]pyrazol]-2-ones.

引用

页码：914 / 919

页数：6

共 45 条

[1] Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents [J].

Abdel-Rahman, AH ;

Keshk, EM ;

Hanna, MA ;

El-Bady, SM .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) :2483-2488

[2]

ABDELLATIF FF, 1990, Z NATURFORSCH B, V45, P1675

[3] Synthesis and molluscicidal activity of new chromene and pyrano[2,3-c]pyrazole derivatives [J].

Abdelrazek, Fathy M. ;

Metz, Peter ;

Kataeva, Olga ;

Jaeger, Anne ;

El-Mahrouky, Sherif F. .

ARCHIV DER PHARMAZIE, 2007, 340 (10) :543-548

[4] Synthesis and molluscicidal activity of new cinnoline and pyrano [2,3-c]pyrazole derivatives [J].

Abdelrazek, Fathy M. ;

Metz, Peter ;

Metwally, Nadia H. ;

El-Mahrouky, Sherif F. .

ARCHIV DER PHARMAZIE, 2006, 339 (08) :456-460

[5] TRICYCLIC HETEROAROMATIC SYSTEMS - SYNTHESIS AND A(1) AND A(2A) ADENOSINE BINDING ACTIVITIES OF SOME 1-ARYL-1,4-DIHYDRO-3-METHYL[1]BENZOPYRANO[2,3-C]PYRAZOL-4-ONES, 1-ARYL-4,9-DIHYDRO-3-METHYL-1H-PYRAZOLO[3,4-B]QUINOLIN-4-ONES, AND 1-ARYL-1H-IMIDAZO[4,5-B]QUINOXALINES [J].

CATARZI, D ;

CECCHI, L ;

COLOTTA, V ;

FILACCHIONI, G ;

MARTINI, C ;

TACCHI, P ;

LUCACCHINI, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (08) :1330-1336

[6] Synthesis and A1 and A2A adenosine binding activity of some pyrano[2,3-c]pyrazol-4-ones [J].

Colotta, V ;

Catarzi, D ;

Varano, F ;

Melani, F ;

Filacchioni, G ;

Cecchi, L ;

Trincavelli, L ;

Martini, C ;

Lucacchini, A .

FARMACO, 1998, 53 (03) :189-196

[7] Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

[8]

Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO

[9]

2-U

[10] Isobutyraldehyde in the synthesis of isopropyl-substituted 4H-pyrans, 1,4-dihydropyrano[2,3-c]pyrazole, 1,4-dihydropyridines, and cyclobutane [J].

Dyachenko, VD ;

Chernega, AN .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2005, 75 (06) :952-960

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