Synthesis of 2,4,5-triarylated imidazoles via three-component domino reaction under catalyst-free conditions

被引:14
作者
Chen, Yang [2 ]
Wang, Ren [3 ]
Ba, Feifei [2 ]
Hou, Junli [2 ]
Ding, Aishun [1 ]
Zhou, Mingdong [2 ]
Guo, Hao [1 ]
机构
[1] Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China
[2] Liaoning Shihua Univ, Sch Chem & Mat Sci, Dandong Rd 1, Fushun 113001, Peoples R China
[3] Shanghai Jiao Tong Univ, Affiliated Peoples Hosp 6, Shanghai Inst Ultrasound Med, Dept Ultrasound Med, Shanghai 200233, Peoples R China
基金
对外科技合作项目(国际科技项目);
关键词
Three-component domino reaction; Imidazole; Catalyst-free; Synthesis; Green chemistry; ONE-POT SYNTHESIS; 2,4,5-TRISUBSTITUTED IMIDAZOLES; MICROWAVE IRRADIATION; EFFICIENT; 2,4,5-TRIARYLIMIDAZOLES; DERIVATIVES; INHIBITORS;
D O I
10.1016/j.jscs.2016.03.001
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A one-pot synthesis of 2,4,5-triarylated imidazoles via three-component domino reaction of 2,2-dibromo-1,2-diarylethanones, ammonium acetate, and aryl aldehydes under catalyst-free conditions is developed. The scope of this reaction is studied. A possible mechanism is proposed based on experimental results. (C) 2016 King Saud University. Production and hosting by Elsevier B.V.
引用
收藏
页码:76 / 81
页数:6
相关论文
共 35 条
[1]  
Abdel-Aty A., 2009, J AGR SCI, V5, P105
[2]  
[Anonymous], 2008, TETRAHEDRON LETT, DOI DOI 10.1016/J.TETLET.2008.02.053
[3]   Synthesis and biological activity of vicinal diaryl-substituted 1H-imidazoles [J].
Bellina, Fabio ;
Cauteruccio, Silvia ;
Rossi, Renzo .
TETRAHEDRON, 2007, 63 (22) :4571-4624
[4]   One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles Using MoO3/SiO2, an Efficient and Recyclable Catalyst [J].
Bhosale, Sidhanath V. ;
Kalyankar, Mohan B. ;
Nalage, Santosh V. ;
Bhosale, Dattatry S. ;
Pandhare, Swati L. ;
Kotbagi, Trupti V. ;
Umbarkar, Shubhangi B. ;
Dongare, Mohan K. .
SYNTHETIC COMMUNICATIONS, 2011, 41 (05) :762-769
[5]   Substituted imidazoles as glucagon receptor antagonists [J].
Chang, LL ;
Sidler, KL ;
Cascieri, MA ;
de Laszlo, S ;
Koch, G ;
Li, B ;
MacCoss, M ;
Mantlo, N ;
O'Keefe, S ;
Pang, M ;
Rolando, A ;
Hagmann, WK .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (18) :2549-2553
[6]   Metal-Free, Acid-Promoted Synthesis of Imidazole Derivatives via a Multicomponent Reaction [J].
Chen, Chung-Yu ;
Hu, Wan-Ping ;
Yan, Pi-Cheng ;
Senadi, Gopal Chandru ;
Wang, Jeh-Jeng .
ORGANIC LETTERS, 2013, 15 (24) :6116-6119
[7]  
Childs B.F., 1978, J AM CHEM SOC, V100, P651
[8]   A facile, solvent and catalyst free, microwave assisted one pot synthesis of hydrazinyl thiazole derivatives [J].
Chinnaraja, D. ;
Rajalakshmi, R. .
JOURNAL OF SAUDI CHEMICAL SOCIETY, 2015, 19 (02) :200-206
[9]   Experiments in the triazine and the glyoxaline series [J].
Cook, AH ;
Jones, DG .
JOURNAL OF THE CHEMICAL SOCIETY, 1941, :278-282
[10]   Catalyst-free photooxidation of triarylphosphines under aerobic conditions [J].
Ding, Aishun ;
Wang, Yu ;
Rios, Ramon ;
Sun, Jing ;
Li, Han ;
Guo, Hao .
JOURNAL OF SAUDI CHEMICAL SOCIETY, 2015, 19 (06) :706-709