Synthesis of 6-amino-4-aryl-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles by heterogeneous reusable catalysts

被引：20
作者：
Shaterian, Hamid Reza [1 ]
Kangani, Mehrnoosh [1 ]
机构：
[1] Univ Sistan & Baluchestan, Dept Chem, Fac Sci, Zahedan, Iran
来源：
RESEARCH ON CHEMICAL INTERMEDIATES | 2014年 / 40卷 / 05期
关键词：
Four-component reaction; Solvent-free; 1,4-Dihydropyrano[2,3-c]pyrazoles; Ethyl acetoacetate; Arylaldehydes; Malononitrile; ONE-POT SYNTHESIS; MULTICOMPONENT SYNTHESIS; SULFURIC-ACID; PYRANOPYRAZOLES; EFFICIENT; CELLULOSE; ALUMINA;
D O I：
10.1007/s11164-013-1097-0
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new, efficient and environmentally benign protocol for the one-pot, four-component synthesis of 1,4-dihydropyrano[2,3-c]pyrazoles by reaction of hydrazine monohydrate, ethyl acetoacetate, arylaldehydes and malononitrile in the presence of a green catalytic amount of P2O5/SiO2, H3PO4/Al2O3, cellulose sulfuric acid and starch sulfuric acid is described. The use of non-toxic and inexpensive materials, simple and clean work-up, short reaction times and good yields of the products are the advantages of this method.
引用
收藏
页码：1997 / 2005
页数：9
相关论文
共 23 条
[1]   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
[2]   Nanosized magnesium oxide as a highly effective heterogeneous base catalyst for the rapid synthesis of pyranopyrazoles via a tandem four-component reaction [J].
Babaie, Maryam ;
Sheibani, Hassan .
ARABIAN JOURNAL OF CHEMISTRY, 2011, 4 (02) :159-162
[3]   Greener approach towards the facile synthesis of 1,4-dihydropyrano[2,3-c]pyrazol-5-yl cyanide derivatives at room temperature [J].
Balaskar, Ravi S. ;
Gavade, Sandip N. ;
Mane, Madhav S. ;
Shingate, Bapurao B. ;
Shingare, Murlidhar S. ;
Mane, Dhananjay V. .
CHINESE CHEMICAL LETTERS, 2010, 21 (10) :1175-1179
[4]  
El-Tamany ESH, 1999, J SERB CHEM SOC, V64, P9
[5]   Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3-c]pyrazoles [J].
Gogoi, Sanjib ;
Zhao, Cong-Gui .
TETRAHEDRON LETTERS, 2009, 50 (19) :2252-2255
[6]  
Hasaninejad A, 2008, ARKIVOC, P64
[7]  
Ismail Z.H., 2003, EGYPT J BIOTECHNOL, V13, P73
[8]   SYNTHESES WITH NITRILES, .35. REACTIONS OF TETRACYANOETHYLENE WITH HETEROCYCLIC-COMPOUNDS [J].
JUNEK, H ;
AIGNER, H .
CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (03) :914-921
[9]   Solvent-free multicomponent synthesis of pyranopyrazoles: per-6-amino-β-cyclodextrin as a remarkable catalyst and host [J].
Kanagaraj, Kuppusamy ;
Pitchumani, Kasi .
TETRAHEDRON LETTERS, 2010, 51 (25) :3312-3316
[10]   Cellulose sulfuric acid: An efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of aryl-14H-dibenzo[a.j]xanthenes under solvent-free conditions [J].
Madhav, J. Venu ;
Reddy, Y. Thirupathi ;
Reddy, P. Narsimha ;
Reddy, M. Nikhil ;
Kuarm, Suresh ;
Crooks, Peter A. ;
Rajitha, B. .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2009, 304 (1-2) :85-87
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