One pot four-component reaction for the efficient synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-3′-carboxylate derivatives

被引：45

作者：

Pal, Suman ^{[1
]}

Khan, Md. Nasim ^{[1
]}

Karamthulla, Shaik ^{[1
]}

Abbas, Sk Jahir ^{[1
]}

Choudhury, Lokman H. ^{[1
]}

机构：

[1] Indian Inst Technol Patna, Dept Chem, Patna 800013, Bihar, India

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 40期

关键词：

Multicomponent reaction; Domino reaction; Isatin; Malononitrile; Hydrazine hydrate; Dialkyl acetylenedicarboxylate; MAMMALIAN-CELL CYCLE; MULTICOMPONENT REACTIONS; MOLLUSCICIDAL ACTIVITY; 3-COMPONENT SYNTHESIS; FACILE ACCESS; CONSTRUCTION; REARRANGEMENT; BISPIROOXINDOLES; STEREOCENTERS; DISCOVERY;

D O I：

10.1016/j.tetlet.2013.07.117

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel one pot protocol has been developed to synthesize various spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-3'-carboxylate derivatives from the four-component reaction of isatin, malononitrile, hydrazine derivatives and dialkyl acetylenedicarboxylates. In this process two C-C bonds, two C-N bonds and one C-O bond have formed in one pot. The notable features of this protocol are simple and environmentally benign reaction condition, easy isolation of products, applicable to a wide range of readily available starting materials and good yields. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5434 / 5440

页数：7

共 37 条

[1] 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

[2] 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

[3] Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products [J].

Antonchick, Andrey P. ;

Gerding-Reimers, Claas ;

Catarinella, Mario ;

Schuermann, Markus ;

Preut, Hans ;

Ziegler, Slava ;

Rauh, Daniel ;

Waldmann, Herbert .

NATURE CHEMISTRY, 2010, 2 (09) :735-740

[4] Highly regioselective synthesis of spirocyclic compounds by a palladium-catalyzed intermolecular tandem reaction [J].

Bi, Hai-Peng ;

Liu, Xue-Yuan ;

Gou, Ta-Rong ;

Guo, Li-Na ;

Duan, Xin-Hua ;

Shu, Xing-Zhong ;

Liang, Yong-Min .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (37) :7068-7071

[5] Amberlyst A21 Catalyzed Chromatography-Free Method for Multicomponent Synthesis of Dihydropyrano[2,3-c]pyrazoles in Ethanol [J].

Bihani, Manisha ;

Bora, Pranjal P. ;

Bez, Ghanashyam ;

Askari, Hassan .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (04) :440-447

[6] A new rearrangement of spiro[indane-1,3′-thiophene] and spiro[naphthalene-1,3′-thiophene] derivatives accompanied by opening of the cycloalkane ring [J].

Bogdanowicz-Szwed, Krystyna ;

Budzowski, Artur ;

Gil, Regina ;

Serda, Pawel .

MONATSHEFTE FUR CHEMIE, 2010, 141 (01) :63-74

[7] CYCLOPIAMINES-A AND CYCLOPIAMINES-B NOVEL OXINDOLE METABOLITES OF PENICILLIUM-CYCLOPIUM WESTLING [J].

BOND, RF ;

BOEYENS, JCA ;

HOLZAPFEL, CW ;

STEYN, PS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (07) :1751-1761

[8] Recent advances in the chemistry of imine-based multicomponent reactions (MCRs) [J].

Choudhury, Lokman H. ;

Parvin, Tasneem .

TETRAHEDRON, 2011, 67 (43) :8213-8228

[9] Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

JOURNAL OF ANTIBIOTICS, 1996, 49 (08) :832-835

[10] Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

TETRAHEDRON, 1996, 52 (39) :12651-12666

← 1 2 3 4 →