Synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles using disulfonic acid imidazolium chloroaluminate as a dual and heterogeneous catalyst

被引：82

作者：

Moosavi-Zare, Ahmad Reza ^{[1
]}

Zolfigol, Mohammad Ali ^{[2
]}

Noroozizadeh, Ehsan ^{[2
]}

Tavasoli, Mahsa ^{[2
]}

Khakyzadeh, Vahid ^{[2
]}

Zare, Abdolkarim ^{[3
]}

机构：

[1] Univ Sayyed Jamaleddin Asadabadi, Asadabad 6541835583, Iran

[2] Bu Ali Sina Univ, Fac Chem, Hamadan 6517838683, Iran

[3] Payame Noor Univ, Dept Chem, Tehran, Iran

来源：

NEW JOURNAL OF CHEMISTRY | 2013年 / 37卷 / 12期

关键词：

HIGHLY EFFICIENT CATALYST; 4 COMPONENT SYNTHESIS; HYDROGEN SULFATE; IONIC LIQUIDS; ONE-POT; RECYCLABLE CATALYST; TRITYL CHLORIDE; RAPID SYNTHESIS; SOLVENT; NITRATION;

D O I：

10.1039/c3nj00629h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this work, disulfonic acid imidazolium chloroaluminate {[Dsim]AlCl4} is applied as a new acidic and heterogeneous catalyst for green, simple and efficient synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles by the one-pot multi-component condensation of aryl aldehydes with ethyl acetoacetate, malononitrile and hydrazine hydrate at 80 degrees C under solvent-free conditions.

引用

页码：4089 / 4094

页数：6

共 31 条

[1] Synthesis and molluscicidal activity of new cinnoline and pyrano [2,3-c]pyrazole derivatives
Abdelrazek, Fathy M.
Metz, Peter
Metwally, Nadia H.
El-Mahrouky, Sherif F.
[J]. ARCHIV DER PHARMAZIE, 2006, 339 (08) : 456 - 460
[2] Ahluwalia VK, 1997, INDIAN J CHEM B, V36, P88
[3] A Practical Catalyst-Free Synthesis of 6-Amino-4 Alkyl/Aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-carbonitrile in Aqueous Medium
Bihani, Manisha
Bora, Pranjal P.
Bez, Ghanashyam
[J]. JOURNAL OF CHEMISTRY, 2013, 2013
[4] Rapid One-pot, Four Component Synthesis of Pyranopyrazoles Using Heteropolyacid Under Solvent-free Condition
Chavan, Hemant V.
Babar, Santosh B.
Hoval, Rahul U.
Bandgar, Babasaheb P.
[J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (11): : 3963 - 3966
[5] El-Tamany ESH, 1999, J SERB CHEM SOC, V64, P9
[6] Feurer A., PCT Int. Appl., Patent No. [WO 2004009589, 2004009589]
[7] Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2
Hallett, Jason P.
Welton, Tom
[J]. CHEMICAL REVIEWS, 2011, 111 (05) : 3508 - 3576
[8] Catalyst-Free One-Pot Four Component Synthesis of Polysubstituted Imidazoles in Neutral Ionic Liquid 1-Butyl-3-methylimidazolium Bromide
Hasaninejad, Alireza
Zare, Abdolkarim
Shekouhy, Mohsen
Rad, Javad Ameri
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (06): : 844 - 849
[9] SYNTHESES WITH NITRILES, .35. REACTIONS OF TETRACYANOETHYLENE WITH HETEROCYCLIC-COMPOUNDS
JUNEK, H
AIGNER, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (03): : 914 - 921
[10] Sulfonic acid functionalized imidazolium salts/FeCl3 as novel and highly efficient catalytic systems for the synthesis of benzimidazoles at room temperature
Khazaei, A.
Zolfigol, M. A.
Moosavi-Zare, A. R.
Zare, A.
Ghaemi, E.
Khakyzadeh, V.
Asgari, Zh
Hasaninejad, A.
[J]. SCIENTIA IRANICA, 2011, 18 (06) : 1365 - 1371

← 1 2 3 4 →