MgCl2 catalyzed one-pot synthesis of 2-hydroxy-3-((5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)naphthalene-1,4-dione derivatives in EG

被引:26
作者
Fu, Zhijie [1 ]
Qian, Kai [1 ]
Li, Sijun [1 ]
Shen, Tianhua [1 ]
Song, Qingbao [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China
基金
美国国家科学基金会;
关键词
2-Hydroxy-3-((5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)naphthalene-1,4-dione derivatives; One-pot; MgCl2; Ethylene glycol; MULTICOMPONENT REACTIONS; ORGANIC-SYNTHESIS; GREEN;
D O I
10.1016/j.tetlet.2016.01.089
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A green and convenient synthetic method has been described for the synthesis of 2-hydroxy-3-((5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)naphthalene-1,4-dione derivatives by a one-pot, four-component reaction of aromatic aldehydes, 2-hydroxy-1,4-naphthoquinone, hydrazine derivatives, and ethyl acetoacetate catalyzed by MgCl2 in ethylene glycol. Simplicity, short reaction time, high yield, and an eco-friendly catalyst are the main advantages of this method. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1104 / 1108
页数:5
相关论文
共 26 条
[1]   Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents [J].
Bashir, Rafia ;
Ovais, Syed ;
Yaseen, Shafiya ;
Hamid, Hinna ;
Alam, M. S. ;
Samim, Mohammad ;
Singh, Surender ;
Javed, Kalim .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (14) :4301-4305
[2]   Synthesis and biological activity of N,N-dialkylaminoalkyl-substituted bisindolyl and diphenyl pyrazolone derivatives [J].
Braña, MF ;
Gradillas, A ;
Ovalles, AG ;
López, B ;
Acero, N ;
Llinares, F ;
Mingarro, DM .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (01) :9-16
[3]   Catalyst-Free One-Pot Access to 3-Pyrazolylisoindolinone Derivatives [J].
Che, Fengfeng ;
Fu, Zhijie ;
Shen, Tianhua ;
Lin, Yan ;
Song, Qingbao .
SYNTHESIS-STUTTGART, 2015, 47 (21) :3403-3411
[4]   Synthesis of 2-(3-amino-2-oxoindolin-3-yl)3-hydroxynaphthalene-1,4-dione derivatives via a one-pot, three-component reaction under catalyst-free conditions [J].
Che, Fengfeng ;
Wang, Yongsheng ;
Shen, Tianhua ;
An, Xiaoxia ;
Song, Qingbao .
COMPTES RENDUS CHIMIE, 2015, 18 (06) :607-610
[5]   Recent advances in the chemistry of imine-based multicomponent reactions (MCRs) [J].
Choudhury, Lokman H. ;
Parvin, Tasneem .
TETRAHEDRON, 2011, 67 (43) :8213-8228
[6]   Multicomponent reactions: advanced tools for sustainable organic synthesis [J].
Cioc, Razvan C. ;
Ruijter, Eelco ;
Orru, Romano V. A. .
GREEN CHEMISTRY, 2014, 16 (06) :2958-2975
[7]  
Daniele C., 2008, Bioorg. Med Chem, V16, P8587
[8]   Recent advances in the synthesis of pyrroles by multicomponent reactions [J].
Estevez, Veronica ;
Villacampa, Mercedes ;
Menendez, J. Carlos .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (13) :4633-4657
[9]   A pyrimidine-pyrazolone nucleoside chimera with potent in vitro anti-orthopoxvirus activity [J].
Fan, Xuesen ;
Zhang, Xinying ;
Zhou, Longhu ;
Keith, Kathy A. ;
Kern, Earl R. ;
Torrence, Paul F. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (12) :3224-3228
[10]   Preparation of 1-(4-methoxyphenyl)-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-ones as potent, selective and bioavailable inhibitors of coagulation factor Xa [J].
Fevig, John M. ;
Cacciola, Joseph ;
Buriak, Joseph, Jr. ;
Rossi, Karen A. ;
Knabb, Robert M. ;
Luettgen, Joseph M. ;
Wong, Pancras C. ;
Bai, Stephen A. ;
Wexler, Ruth R. ;
Lam, Patrick Y. S. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (14) :3755-3760