Synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles in water using p-dodecylbenzenesulfonic acid as catalyst

被引:43
作者
Das, Biswanath [1 ]
Kashanna, Jajula [1 ]
Kumar, Rathod Aravind [1 ]
Jangili, Paramesh [1 ]
机构
[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
来源
MONATSHEFTE FUR CHEMIE | 2013年 / 144卷 / 02期
关键词
Substituted imidazole; p-Dodecylbenzenesulfonic acid; Ketones; One-pot synthesis; Heterocycles; Green chemistry; ONE-POT SYNTHESIS; TETRASUBSTITUTED-IMIDAZOLES; EFFICIENT SYNTHESIS; BIOLOGICAL-ACTIVITY; 1,2-DIKETONES; ALDEHYDES; IODINE;
D O I
10.1007/s00706-012-0770-0
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2,4,5-Trisubstituted imidazoles have been synthesized by treatment of benzil with aldehydes and ammonium acetate in water under reflux in the presence of p-dodecylbenzenesulfonic acid as catalyst. The same reaction using an additional amine affords 1,2,4,5-tetrasubstituted imidazoles. The products are formed in high yields within 4 h under eco-friendly conditions.
引用
收藏
页码:223 / 226
页数:4
相关论文
共 33 条
[1]   Continuous synthesis of tri- and tetrasubstituted imidazoles via a multicomponent reaction under microreactor conditions [J].
Acke, Davy R. J. ;
Orru, Romano V. A. ;
Stevens, Christian V. .
QSAR & COMBINATORIAL SCIENCE, 2006, 25 (5-6) :474-483
[2]  
Alamgir M, 2007, TOP HETEROCYCL CHEM, V9, P87, DOI 10.1007/7081_2007_088
[3]  
Ali J, 2011, E-J CHEM, V8, P547
[4]   Analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole as potential antibacterial agents. [J].
Antolini, M ;
Bozzoli, A ;
Ghiron, C ;
Kennedy, G ;
Rossi, T ;
Ursini, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) :1023-1028
[5]   An alternative synthesis of benzobis(imidazolium) salts via a 'one-pot' cyclization/oxidation reaction sequence [J].
Boydston, Andrew J. ;
Khramov, Dimitri M. ;
Bielawski, Christopher W. .
TETRAHEDRON LETTERS, 2006, 47 (29) :5123-5125
[6]  
Das B., 2010, Synth. Commun, V40, P2667, DOI DOI 10.1080/00397910903318633
[7]   Hypervalent iodine-mediated efficient synthesis of imidazoles [J].
Das, Biswanath ;
Srinivas, Yallamalla ;
Holla, Harish ;
Krishnaiah, Maddeboina ;
Narender, Ravirala .
CHEMISTRY LETTERS, 2007, 36 (10) :1270-1271
[8]   An Efficient Multicomponent Synthesis of Polysubstituted Pyrrolidines and Tetrahydropyrimidines Starting Directly from Nitro Compounds in Water [J].
Das, Biswanath ;
Shinde, Digambar Balaji ;
Kanth, Boddu Shashi ;
Satyalakshmi, Gandham .
SYNTHESIS-STUTTGART, 2010, (16) :2823-2827
[9]   Organic Reactions in Water: A Distinct Novel Approach for an Efficient Synthesis of α-Amino Phosphonates Starting Directly from Nitro Compounds [J].
Das, Biswanath ;
Satyalakshmi, Gandham ;
Suneel, Kanaparthy ;
Damodar, Kongara .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8400-8402
[10]   An Efficient, One-Pot, Multicomponent Synthesis of β-Acetamido Carbonyl Compounds Using Cyanuric Chloride in an Aqueous Medium [J].
Das, Biswanth ;
Srilatha, Malampati ;
Veeranjaneyulu, Boyapati ;
Rao, Bethapudi Rama .
SYNTHESIS-STUTTGART, 2010, (05) :803-806