Ultrasound-Promoted Mild, and Efficient Protocol for Three-Component Synthesis of 2,4,5-Trisubstituted Imidazoles Using Urea and PPh3as the Sources of Nitrogen and Organocatalyst

被引:18
作者
Behrouz, Somayeh [1 ]
Navid Soltani Rad, Mohammad [1 ]
Abdollahzadeh, Mahla [1 ]
Amin Piltan, Mohammad [1 ]
机构
[1] Shiraz Univ Technol, Dept Chem, Med Chem Res Lab, Shiraz 71555313, Iran
关键词
Heterocycles; Organocatalysis; Triphenylphosphine; Ultrasound; Urea; ONE-POT SYNTHESIS; HIGHLY EFFICIENT; CATALYST; GREEN; BOND; ANTIBACTERIAL; DERIVATIVES; ANTIFUNGAL; BENIGN; ACIDS;
D O I
10.1002/slct.202001722
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Substituted imidazoles have wild applications in different area of sciences and industries. In this research, the catalytic activity of PPh(3)as a cheap and efficient organocatalyst is reported for synthesis of 2,4,5-trisubstituted imidazoles. In this method, ultrasonic assisted one-pot, three-component reaction of benzil, aldehydes, urea and PPh(3)in ethylene glycol as a green solvent at room temperature has been achieved to afford the structurally diverse 2,4,5-trisubstituted imidazoles in 80-95 %. The effect of different parameters on the reaction progress was also discussed. Utilizing ultrasonic irradiation dramatically improved the reaction in terms of yields and reaction times compared to conventional heating technique. The current protocol offers many advantages such as mild reaction conditions, short reaction time, the use of non-metallic, harmless, and cheap catalyst, ease of separation and purification, simple work-up procedure, and the reactivity to all types of aldehydes particularly the aliphatic aldehydes.
引用
收藏
页码:7467 / 7473
页数:7
相关论文
共 51 条
[1]  
ABRAHAMS SL, 1989, J PHARMACOL EXP THER, V249, P359
[2]  
[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[3]  
[Anonymous], 2011, Handbook on Applications of Ultrasound
[4]   TERTIARY PHOSPHANE-TETRACHLOROMETHANE, A VERSATILE REAGENT FOR CHLORINATION, DEHYDRATION, AND P-N LINKAGE [J].
APPEL, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (12) :801-811
[5]  
Appel R., 1975, Angew. Chem, V87, P863
[6]   Microwave-assisted facile and convenient synthesis of fatty acid amide (erucamide): Chemical-catalyzed rapid method [J].
Awasthi, Neeraj Praphulla ;
Singh, Rajinder Pal .
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, 2009, 111 (02) :202-206
[7]   A novel and efficient Lewis acid catalysed preparation of pyrimidines:: Microwave-promoted reaction of urea and β-formyl enamides [J].
Barthakur, Madan G. ;
Borthakur, Moyurima ;
Devi, Prarthana ;
Saikia, Chandan J. ;
Saikia, Anil ;
Bora, Utpal ;
Chetia, Apurba ;
Boruah, Romesh C. .
SYNLETT, 2007, (02) :223-226
[8]   Chitosan-silica sulfate nanohybrid: a highly efficient and green heterogeneous nanocatalyst for the regioselective synthesis of N-alkyl purine, pyrimidine and related N-heterocycles via presilylated method [J].
Behrouz, Somayeh ;
Rad, Mohammad Navid Soltani ;
Piltan, Mohammad Amin .
CHEMICAL PAPERS, 2020, 74 (01) :113-124
[9]   Ultrasound promoted rapid and green synthesis of thiiranes from epoxides in water catalyzed by chitosan-silica sulfate nano hybrid (CSSNH) as a green, novel and highly proficient heterogeneous nano catalyst [J].
Behrouz, Somayeh ;
Rad, Mohammad Navid Soltani ;
Piltan, Mohammad Amin .
ULTRASONICS SONOCHEMISTRY, 2018, 40 :517-526
[10]   Chitosan-Silica Sulfate Nano Hybrid as a Novel and Highly Proficient Heterogeneous Nano Catalyst for Regioselective Ring Opening of Epoxides via Carboxylic Acids [J].
Behrouz, Somayeh ;
Rad, Mohammad Navid Soltani ;
Piltan, Mohammad Amin ;
Doroodmand, Mohammad Mahdi .
HELVETICA CHIMICA ACTA, 2017, 100 (09)