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

被引:16
|
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 50 条
  • [1] A green, catalyst-free synthesis of pyrazolopyranopyrimidines in polyethylene glycol as a biodegradable medium at ambient temperature
    Rezvan Kardooni
    Ali Reza Kiasat
    Molecular Diversity, 2019, 23 : 639 - 649
  • [2] A green, catalyst-free synthesis of pyrazolopyranopyrimidines in polyethylene glycol as a biodegradable medium at ambient temperature
    Kardooni, Rezvan
    Kiasat, Ali Reza
    MOLECULAR DIVERSITY, 2019, 23 (03) : 639 - 649
  • [3] Catalyst-free, a Green, and Efficient Protocol for the Synthesis of 1,8-dioxooctahydroxanthenes in Magnetized Water
    Bakherad, Mohammad
    Keivanloo, Ali
    Amin, Amir Hossein
    Farkhondeh, Amir
    JOURNAL OF THE MEXICAN CHEMICAL SOCIETY, 2019, 63 (04) : 199 - 207
  • [4] Simple Catalyst-Free Method to the Synthesis of β-SiC Nanowires and Their Field Emission Properties
    Yang, G. Z.
    Cui, H.
    Sun, Y.
    Gong, L.
    Chen, J.
    Jiang, D.
    Wang, C. X.
    JOURNAL OF PHYSICAL CHEMISTRY C, 2009, 113 (36): : 15969 - 15973
  • [5] A green, simple, catalyst-free, and efficient method for electro-organic synthesis of new benzofuran derivatives
    Alireza Asghari
    Anahita Gholami
    Mohammad Bakherad
    Mohsen Ameri
    Journal of the Iranian Chemical Society, 2017, 14 : 2127 - 2133
  • [6] A green, simple, catalyst-free, and efficient method for electro-organic synthesis of new benzofuran derivatives
    Asghari, Alireza
    Gholami, Anahita
    Bakherad, Mohammad
    Ameri, Mohsen
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2017, 14 (10) : 2127 - 2133
  • [7] Simple and catalyst-free method for the synthesis of diaryl selenides by reactions of arylselenols and arenediazonium salts
    Balaguez, Renata A.
    Ricordi, Vanessa Gentil
    Freitas, Camilo S.
    Perin, Gelson
    Schumacher, Ricardo F.
    Alves, Diego
    TETRAHEDRON LETTERS, 2014, 55 (05) : 1057 - 1061
  • [8] Simple and catalyst-free synthesis of silicon oxide nanowires and nanocoils
    Chen, Xinqi
    Ruoff, Rodney S.
    NANO, 2007, 2 (02) : 91 - 95
  • [9] Catalyst-free Multicomponent Synthesis of β-Mercapto Diketones in Water
    Li Li
    Liu Bokai
    Wu Qi
    Lin Xianfu
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (09) : 1856 - 1862
  • [10] Synthesis of tetraketones in water and under catalyst-free conditions
    Yu, Jian-Jun
    Wang, Li-Min
    Liu, Jin-Qian
    Guo, Feng-Lou
    Liu, Ying
    Jiao, Ning
    GREEN CHEMISTRY, 2010, 12 (02) : 216 - 219