Tributylhexadecylphosphonium bromide: an efficient reagent system for the one-pot synthesis of 2,4,5-trisubstituted imidazoles

被引:5
作者
Heidari, Mohammad [1 ]
Rezaei, Mohsen [2 ]
Badri, Rashid [1 ]
机构
[1] Islamic Azad Univ, Coll Sci, Dept Chem, Ahvaz Branch, Ahvaz, Iran
[2] Ahvaz Jundishapur Univ Med Sci, Sch Pharm, Dept Pharmacol & Toxicol, Ahvaz, Iran
关键词
2,4,5-trisubstituted imidazoles; aldehyde; benzil; homogeneous catalysis; one-pot synthesis; ALDEHYDES; 1,2-DIKETONES; CATALYST;
D O I
10.1515/hc-2014-0182
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of benzil, an aromatic aldehyde, and ammonium acetate in ethanol at reflux in the presence of tributylhexadecylphosphonium bromide as catalyst affords a 2,4,5-trisubstituted imidazole. The present methodology offers several advantages over the literature methods, including excellent yields, shorter reaction times, environmentally benign milder reaction conditions, cost-effectiveness of catalyst, easy workup, and purification of products by nonchromatographic methods.
引用
收藏
页码:73 / 76
页数:4
相关论文
共 21 条
[1]   Zeolite HY and silica gel as new and efficient heterogenous catalysts for the synthesis of triarylimidazoles under microwave irradiation [J].
Balalaie, S ;
Arabanian, A ;
Hashtroudi, MS .
MONATSHEFTE FUR CHEMIE, 2000, 131 (09) :945-948
[2]   Tetrabutylammonium bromide (TBAB) in isopropanol: An efficient, novel, neutral and recyclable catalytic system for the synthesis of 2,4,5-trisubstituted imidazoles [J].
Chary, Mahankhali Venu ;
Keerthysri, Nallani Chakravarthula ;
Vupallapati, Srinivasu V. N. ;
Lingaiah, N. ;
Kantevari, Srinivas .
CATALYSIS COMMUNICATIONS, 2008, 9 (10) :2013-2017
[3]  
Gharib A, 2014, BULG CHEM COMMUN, V46, P165
[4]   Synthesis of 2,4,5-triaryl-imidazoles catalyzed by NiCl2•6H2O under heterogeneous system [J].
Heravi, Majid M. ;
Bakhtiari, Khadijeh ;
Oskooie, Hossein A. ;
Taheri, Shima .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 263 (1-2) :279-281
[5]   MCM-41 Mesoporous Silica: Efficient and Reusable Catalyst for the Synthesis of 2,4,5-Trisubstituted Imidazoles Under Solvent-Free Conditions [J].
Heravi, Majid M. ;
Zakeri, Masoumeh ;
Haghi, Hoda .
SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2011, 41 (10) :1310-1314
[6]   Highly efficient and eco-friendly synthesis of 2-alkyl and 2-aryl-4,5-dipheny1-1H-imidazoles under mild conditions [J].
MaGee, David I. ;
Bahramnejad, M. ;
Dabiri, Minoo .
TETRAHEDRON LETTERS, 2013, 54 (21) :2591-2594
[7]  
Marzouk A A., 2013, World Journal of Organic Chemistry, V1, P6, DOI [DOI 10.HTTPS://D0I.0RG/10.12691, 10.12691/wjoc-1-1-2, DOI 10.12691/WJOC-1-1-2]
[8]  
Newman MJ, 2000, CANCER RES, V60, P2964
[9]   L-Proline: an efficient catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles [J].
Samai, Subhasis ;
Nandi, Ganesh Chandra ;
Singh, Pallavi ;
Singh, M. S. .
TETRAHEDRON, 2009, 65 (49) :10155-10161
[10]   Imidazole libraries on solid support [J].
Sarshar, S ;
Siev, D ;
Mjalli, AMM .
TETRAHEDRON LETTERS, 1996, 37 (06) :835-838