[Bu3NH] [HSO4] catalyzed: an eco-efficient synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions

被引:31
作者
Shaikh, Mohd Akmal [1 ]
Farooqui, Mazahar [2 ]
Abed, Syed [3 ]
机构
[1] Maulana Azad Coll, Post Grad & Res Ctr, Aurangabad 431001, Maharashtra, India
[2] Dr Rafiq Zakaria Coll Women, Aurangabad 431001, Maharashtra, India
[3] Govt Coll Arts & Sci, Aurangabad 431001, Maharashtra, India
关键词
Bronsted acidic ionic liquids; Bu3NH][HSO4; 1H-pyrazolo[1,2-b]phthalazine-5,10-diones; 2H-indazolo [2,1-b]phthalazine-triones; Sustainable techniques; IONIC LIQUIDS;
D O I
10.1007/s11164-018-3435-8
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Bronsted acidic ionic liquid [Bu3NH][HSO4] as an eco-efficient catalyst for the one-pot multicomponent synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and 2H-indazolo[2,1-b]phthalazine-triones by using various aldehyde, malononitrile/dimedone, and phthalhydrazide in the absence of a solvent at 80 degrees C is described. Further, the catalyst is prepared from readily available reagents and fully characterized by different techniques such as FT-IR, H-1-NMR, C-13-NMR, and TG, DTG and DTA analyses. The current synthetic protocol offers the mild reaction conditions, short reaction times (9-30 min), excellent yields of the products (83-95%), a clean and straightforward work-up, reusability of the catalyst up to seven catalytic runs, and a sustainable alternative to the existing methods.
引用
收藏
页码:5483 / 5500
页数:18
相关论文
共 55 条
[1]  
Al-Assar F., 2002, Pharm. Chem. J., V36, P598, DOI [10.1023/A:1022665331722, DOI 10.1023/A:1022665331722]
[2]   Green Chemistry: Principles and Practice [J].
Anastas, Paul ;
Eghbali, Nicolas .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312
[3]  
Atashkar B., 2015, RES CHEM INTERMEDIAT, V41, P6
[4]   Urea-functionalized silica-coated Fe3-xTixO4 magnetic nanoparticles: as highly efficient and recyclable heterogeneous nanocatalyst for synthesis of 4H-chromene and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives [J].
Azarifar, Davood ;
Badalkhani, Omolbanin ;
Abbasi, Younes ;
Hasanabadi, Morteza .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2017, 14 (02) :403-418
[5]   3-phenyl-6-(2-pyridyl)methyloxy-1,2,4-triazolo[3,4-α]phthalazines and analogues:: High-affinity γ-aminobutyric acid-A benzodiazepine receptor ligands with α2, α3, and α5-subtype binding selectivity over α1 [J].
Carling, RW ;
Moore, KW ;
Street, LJ ;
Wild, D ;
Isted, C ;
Leeson, PD ;
Thomas, S ;
O'Connor, D ;
McKernan, RM ;
Quirk, K ;
Cook, SM ;
Atack, JR ;
Wafford, KA ;
Thompson, SA ;
Dawson, GR ;
Ferris, P ;
Castro, JL .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (07) :1807-1822
[6]   Quaternary Ammonium Ionic Liquid Electrolyte for a Silicon Nanowire-Based Lithium Ion Battery [J].
Chakrapani, Vidhya ;
Rusli, Florencia ;
Filler, Micheal A. ;
Kohl, Paul A. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2011, 115 (44) :22048-22053
[7]  
Chate A. V., 2017, CHINESE CHEM LETT, V28, P7
[8]   Novel bronsted acidic ionic liquids and their use as dual solvent-catalysts [J].
Cole, AC ;
Jensen, JL ;
Ntai, I ;
Tran, KLT ;
Weaver, KJ ;
Forbes, DC ;
Davis, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :5962-5963
[9]   Room temperature dialkylimidazolium ionic liquid-based fuel cells [J].
de Souza, RF ;
Padilha, JC ;
Gonçalves, RS ;
Dupont, J .
ELECTROCHEMISTRY COMMUNICATIONS, 2003, 5 (08) :728-731
[10]  
Ganeshpure P.A., 2007, ARKIVOC, V2007