SYNTHESIS OF 3-(3-METHYL-1-ARYL-1H-PYRAZOL-5-YL)-2H-2-CHROMEN-2-ONE DERIVATIVES VIA A ONE-POT, THREE-COMPONENT REACTION

被引:8
作者
Alizadeh, Abdolali [1 ]
Ghanbaripour, Rashid [1 ]
机构
[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
关键词
Arylhydrazine; coumarin; 4-hydroxy-6-methyl-2H-pyran-2-one; pyrazole; salicylaldehyde; COUMARIN DERIVATIVES; BINDING-SITE; INHIBITORS; COMPLEXES; CATALYST; PYRAZOLE; LIGANDS;
D O I
10.1080/00397911.2013.867507
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of 3-(3-methyl-1-aryl-1H-pyrazol-5-yl)-2H-2-chromen-2-one derivatives by the reaction of salicylaldehydes, 4-hydroxy-6-methyl-2H-pyran-2-one, and arylhydrazine in acetonitrile under reflux condition and in the presence of piperidine is reported. This three-component reaction has some advantages such as ease of handling, good yields, and easy purification. All structures were confirmed by infrared, mass, H-1 NMR, and C-13 NMR spectroscopy.
引用
收藏
页码:1635 / 1640
页数:6
相关论文
共 29 条
[1]   CYP2C9 structure-metabolism relationships:: Optimizing the metabolic stability of COX-2 inhibitors [J].
Ahlstroem, Marie M. ;
Ridderstroem, Marianne ;
Zamora, Ismael ;
Luthman, Kristina .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (18) :4444-4452
[2]   An Approach to the Synthesis of 2-Acylchromeno[3,4-c]pyrrol-4(2H)-one Derivatives via a Sequential Three-Component Reaction [J].
Alizadeh, Abdolali ;
Ghanbaripour, Rashid ;
Zhu, Long-Guan .
SYNLETT, 2013, 24 (16) :2124-2126
[3]   A Novel and Efficient Synthesis of 3-[(4,5-Dihydro-1H-pyrrol-3-yl)carbonyl]-2H-chromen-2-ones (=3-[(4,5-Dihydro-1H-pyrrol-3-yl)carbonyl]-2H-1-benzopyran-2-ones) [J].
Alizadeh, Abdolali ;
Ghanbaripour, Rashid .
HELVETICA CHIMICA ACTA, 2013, 96 (03) :473-477
[4]   Synthesis of Heterocyclic [3.3.3]Propellanes via a Sequential Four-Component Reaction [J].
Alizadeh, Abdolali ;
Rezvanian, Atieh ;
Zhu, Long-Guan .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (09) :4385-4390
[5]   Synthesis of some tetrazole fused pyrido[2,3-c]coumarin derivatives from a one-pot three-component reaction via intramolecular 1,3-dipolar cycloaddition reaction of azide to nitriles [J].
Borah, Pallabi ;
Naidu, P. Seetham ;
Bhuyan, Pulak J. .
TETRAHEDRON LETTERS, 2012, 53 (37) :5034-5037
[6]   Design, synthesis and biological evaluation of coumarin alkylamines as potent and selective dual binding site inhibitors of acetylcholinesterase [J].
Catto, Marco ;
Pisani, Leonardo ;
Leonetti, Francesco ;
Nicolotti, Orazio ;
Pesce, Paolo ;
Stefanachi, Angela ;
Cellamare, Saverio ;
Carotti, Angelo .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (01) :146-152
[7]   Tetrahedral zinc complexes with liquid crystalline and luminescent properties:: Interplay between nonconventional molecular shapes and supramolecular mesomorphic order [J].
Cavero, Emma ;
Uriel, Santiago ;
Romero, Pilar ;
Serrano, Jose Luis ;
Gimenez, Raquel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (37) :11608-11618
[8]   Blue-emitting platinum(II) complexes bearing both pyridylpyrazolate chelate and bridging pyrazolate ligands: Synthesis, structures, and photophysical properties [J].
Chang, Sheng-Yuan ;
Chen, Jing-Lin ;
Chi, Yun ;
Cheng, Yi-Ming ;
Lee, Gene-Hsiang ;
Jiang, Chang-Ming ;
Chou, Pi-Tai .
INORGANIC CHEMISTRY, 2007, 46 (26) :11202-11212
[9]  
Durga R., 2007, TETRAHEDRON LETT, V48, P1385
[10]  
Elguero J., 1996, Comprehensive Heterocyclic Chemistry, V5