A green and efficient protocol for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives via a one-pot, four component reaction by grinding method

被引:45
作者
Ambethkar, Sethurajan [1 ]
Padmini, Vediappen [1 ]
Bhuvanesh, Nattamai [2 ]
机构
[1] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai 625021, Tamil Nadu, India
[2] Texas A&M Univ, Dept Chem, Xray Diffract Lab, College Stn, TX 77842 USA
关键词
Pyranopyrazole; Multicomponent; Grinding; Antioxidant; Antimicrobial; MULTICOMPONENT SYNTHESIS; L-PROLINE; BIOLOGICAL EVALUATION; AQUEOUS-MEDIUM; IN-VITRO; CATALYST; PYRANOPYRAZOLES; 4-COMPONENT; WATER; AGENTS;
D O I
10.1016/j.jare.2014.11.011
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
An efficient grinding protocol for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives from acetylene ester, hydrazine hydrate, aryl aldehydes and malononitrile under solvent free conditions has been achieved with excellent yields. The structures of the synthesized compounds were deduced by spectroscopic techniques and the compounds were further evaluated for their in vitro antioxidant and antimicrobial activities. (C) 2014 Production and hosting by Elsevier B.V. on behalf of Cairo University.
引用
收藏
页码:975 / 985
页数:11
相关论文
共 41 条
[1]   Proline confined FAU zeolite: heterogeneous hybrid catalyst for the synthesis of spiroheterocycles via a Mannich type reaction [J].
Arya, Kapil ;
Rajesh, U. Chinna ;
Rawat, Diwan Singh .
GREEN CHEMISTRY, 2012, 14 (12) :3344-3351
[2]   Simple and efficient protocol for the synthesis of novel dihydro-1H-pyrano[2,3-c]pyrazol-6-ones via a one-pot four-component reaction [J].
Azzam, Sadeq Hamood Saleh ;
Pasha, M. A. .
TETRAHEDRON LETTERS, 2012, 53 (50) :6834-6837
[3]  
Bendary E., 2013, Annals of Agricultural Science (Cairo), V58, P173, DOI 10.1016/j.aoas.2013.07.002
[4]   Amberlyst A21 Catalyzed Chromatography-Free Method for Multicomponent Synthesis of Dihydropyrano[2,3-c]pyrazoles in Ethanol [J].
Bihani, Manisha ;
Bora, Pranjal P. ;
Bez, Ghanashyam ;
Askari, Hassan .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (04) :440-447
[5]   Facile and One-Pot Access to Diverse and Densely Functionalized 2-Amino-3-cyano-4H-pyrans and Pyran-Annulated Heterocyclic Scaffolds via an Eco-Friendly Multicomponent Reaction at Room Temperature Using Urea as a Novel Organo-Catalyst [J].
Brahmachari, Goutam ;
Banerjee, Bubun .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2014, 2 (03) :411-422
[6]   Synthesis, antimicrobial, antiquorum-sensing, antitumor and cytotoxic activities of new series of fused [1,3,4]thiadiazoles [J].
El-Gohary, Nadia S. ;
Shaaban, Mona I. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 63 :185-195
[7]   Organocatalysis in Synthesis: L-Proline as an Enantioselective Catalyst in the Synthesis of Pyrans and Thiopyrans [J].
Elnagdi, Noha M. Hilmy ;
Al-Hokbany, Noura Saad .
MOLECULES, 2012, 17 (04) :4300-4312
[8]   Multicomponent reactions in unconventional solvents: state of the art [J].
Gu, Yanlong .
GREEN CHEMISTRY, 2012, 14 (08) :2091-2128
[9]   An expedient four-component domino protocol for the regioselective synthesis of highly functionalized pyranopyrazoles and chromenopyrazoles via nitroketene-N,S-acetal chemistry under solvent-free condition [J].
Jayabal, Kamalraja ;
Paramasivan, Thirumalai Perumal .
TETRAHEDRON LETTERS, 2014, 55 (12) :2010-2014
[10]   Ruthenium(II)/(III) complexes of 4-hydroxy-pyridine-2,6-dicarboxylic acid with PPh3/AsPh3 as co-ligand: Impact of oxidation state and co-ligands on anticancer activity in vitro [J].
Kamatchi, Thangavel Sathiya ;
Chitrapriya, Nataraj ;
Lee, Hyosun ;
Fronczek, Chris F. ;
Fronczek, Frank R. ;
Natarajan, Karuppannan .
DALTON TRANSACTIONS, 2012, 41 (07) :2066-2077