A New, Simple, Catalyst-free Method for the Synthesis of Pyrazolopyranopyrimidines in Magnetized Water

被引:17
作者
Bakherad, Mohammad [1 ]
Doosti, Rahele [1 ]
Keivanloo, Ali [1 ]
Gholizadeh, Mostafa [2 ]
Amin, Amir H. [1 ]
机构
[1] Shahrood Univ Technol, Sch Chem, Shahrood 3619995161, Iran
[2] Ferdowsi Univ Mashhad, Dept Chem, Mashhad 91779, Iran
关键词
Biologically-active compounds; catalyst-free; four-component reaction; magnetized water; pyrazolopyranopyrimidine; promoting medium; ONE-POT SYNTHESIS; LIQUID WATER; 4-COMPONENT SYNTHESIS; DERIVATIVES; GREEN; FIELD; PROTOCOL; SIMULATION; SCAFFOLDS; MECHANISM;
D O I
10.2174/1570178614666170511170329
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Background: The design of biologically-active compounds is a challenging viewpoint in medicinal chemistry, and pyranopyrazoles and pyranopyrimidine play a crucial role as biologically-active molecules. Methods: At the moment, a few examples have been reported for the synthesis of pyrazolopyranopyrimidine derivatives. In this work, magnetized water was applied as a green promoting medium for one-pot, practical, efficient, and environmentally benign four-component reaction of an aldehyde, ethyl acetoacetate, hydrazine hydrate, and thiobarbituric acid under catalyst-free conditions. Results: The reactions proceeded rapidly for aromatic aldehydes with the electron-withdrawing or electron-donating groups at different positions of the ring, and heteroaryl aldehydes, and the desired products were isolated in high yields without any side product formation in very short reaction times. Conclusion: An efficient, catalyst-free, green, and convenient method was proposed for the synthesis of pyrazolopyranopyrimidines in magnetized water in good-to-high yields.. This method offers the advantages of short reaction times, low costs, quantitative yields, simple work-up, green, and no need of any organic solvent.
引用
收藏
页码:510 / 516
页数:7
相关论文
共 33 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]   Efficient one-pot preparation of novel fused chromeno[2,3-d]pyrimidine and pyrano[2,3-d]pyrimidine derivatives [J].
Aly, Hala M. ;
Kamal, Mona M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 47 :18-23
[3]   On reduction in the surface tension of water due to magnetic treatment [J].
Amiri, MC ;
Dadkhah, AA .
COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS, 2006, 278 (1-3) :252-255
[4]   Using magnetized water as a solvent for a green, catalyst-free, and efficient protocol for the synthesis of pyrano[2,3-c]pyrazoles and pyrano[4′,3′: 5,6]pyrazolo [2,3-d]pyrimidines [J].
Bakherad, Mohammad ;
Keivanloo, Ali ;
Gholizadeh, Mostafa ;
Doosti, Rahele ;
Javanmardi, Mohaddese .
RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (02) :1013-1029
[5]   Ultrasound promoted one-pot synthesis of 2-amino-4,8-dihydropyrano [3,2-b]pyran-3-carbonitrile scaffolds in aqueous media: A complementary 'green chemistry' tool to organic synthesis [J].
Banitaba, Sayed Hossein ;
Safari, Javad ;
Khalili, Shiva Dehghan .
ULTRASONICS SONOCHEMISTRY, 2013, 20 (01) :401-407
[6]   The Mechanism of On-Water Catalysis [J].
Beattie, James K. ;
McErlean, Christopher S. P. ;
Phippen, Christopher B. W. .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (30) :8972-8974
[7]   The effects of magnetic fields on water molecular hydrogen bonds [J].
Cai, Ran ;
Yang, Hongwei ;
He, Jinsong ;
Zhu, Wanpeng .
JOURNAL OF MOLECULAR STRUCTURE, 2009, 938 (1-3) :15-19
[8]   Magnetic Field Trapping in Coherent Antisymmetric States of Liquid Water Molecular Rotors [J].
Cefalas, A. C. ;
Sarantopoulou, E. ;
Kollia, Z. ;
Riziotis, C. ;
Drazic, G. ;
Kobe, S. ;
Strazisar, J. ;
Meden, A. .
JOURNAL OF COMPUTATIONAL AND THEORETICAL NANOSCIENCE, 2010, 7 (09) :1800-1805
[9]  
Chen S. V., 1992, PHYSICS CHINA, V2, P109
[10]   Nanocatalytic one-pot, four-component synthesis of some new triheterocyclic compounds consisting of pyrazole, pyran, and pyrimidinone rings [J].
Dastkhoon, Sadegh ;
Tavakoli, Zaiba ;
Khodabakhshi, Saeed ;
Baghernejad, Mojtaba ;
Abbasabadi, Masoud Khaleghi .
NEW JOURNAL OF CHEMISTRY, 2015, 39 (09) :7268-7271