A solvent-free synthesis of 1,2,4,5-tetrasubstituted imidazoles using molecular iodine as catalyst

被引:23
作者
Ren, Yi-Ming [1 ]
Cai, Chun [2 ]
机构
[1] Anhui Univ Technol & Sci, Dept Biochem Engn, Wuhu 241000, Peoples R China
[2] Nanjing Univ Sci & Technol, Chem Engn Coll, Nanjing 210094, Peoples R China
关键词
molecular iodine; 1,2,4,5-tetrasubstituted imidazoles; solvent-free; ONE-POT SYNTHESIS; TETRASUBSTITUTED IMIDAZOLES; MICROWAVE IRRADIATION; CARBONYL-COMPOUNDS; HIGHLY EFFICIENT; 2-IMIDAZOLINES; DERIVATIVES; ALDEHYDES; ALCOHOLS; ACID;
D O I
10.3184/030823410X12659021476402
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient method for the synthesis of 1,2,4,5-tetrasubstituted imidazoles by three-component condensation of benzil, benzonitrile derivatives and primary amines under solvent-free conditions using molecular iodine as catalyst is described with high product yields. The significant features of the iodine-catalysed condensation are operational simplicity, inexpensive reagents, high yield of products and use of non-toxic reagents.
引用
收藏
页码:133 / 134
页数:2
相关论文
共 30 条
[1]   A novel one-pot synthesis of tetrasubstituted imidazoles under solvent-free conditions and microwave irradiation [J].
Balalaie, S ;
Hashemi, MM ;
Akhbari, M .
TETRAHEDRON LETTERS, 2003, 44 (08) :1709-1711
[2]   Samarium-induced iodine-catalyzed reduction of imines: synthesis of amine derivatives [J].
Banik, BK ;
Zegrocka, O ;
Banik, I ;
Hackfeld, L ;
Becker, FF .
TETRAHEDRON LETTERS, 1999, 40 (37) :6731-6734
[3]  
Basu MK, 2002, SYNLETT, P319
[4]   SULPHUR-METHYLENE ISOSTERISM IN DEVELOPMENT OF METIAMIDE, A NEW HISTAMINE H2-RECEPTOR ANTAGONIST [J].
BLACK, JW ;
DURANT, GJ ;
EMMETT, JC ;
GANELLIN, CR .
NATURE, 1974, 248 (5443) :65-67
[5]   Solvent and catalyst free three-component coupling of carbonyl compounds, amines and triethylphosphite;: a new synthesis of α-aminophosphonates [J].
Chandrasekhar, S ;
Narsihmulu, C ;
Sultana, SS ;
Saritha, B ;
Prakash, SJ .
SYNLETT, 2003, (04) :505-506
[6]   An efficient synthesis of tetrasubstituted imidazoles from N-(2-oxo)-amides [J].
Claiborne, CF ;
Liverton, NJ ;
Nguyen, KT .
TETRAHEDRON LETTERS, 1998, 39 (49) :8939-8942
[7]   Studies on novel synthetic methodologies.: Part 126.: Iodine-catalyzed efficient conjugate addition of pyrroles to α,β-unsaturated ketones [J].
Das, Biswanath ;
Chowdhury, Nikhil ;
Damodar, Kongara .
TETRAHEDRON LETTERS, 2007, 48 (16) :2867-2870
[8]   IN SEARCH OF THE DIGITALIS REPLACEMENT [J].
ERHARDT, PW .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (02) :231-237
[9]   SYNTHESIS OF DIPHTHAMIDE - THE TARGET OF DIPHTHERIA-TOXIN CATALYZED ADP-RIBOSYLATION IN PROTEIN-SYNTHESIS ELONGATION FACTOR-II [J].
EVANS, DA ;
LUNDY, KM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1495-1496
[10]   Iodine catalyzes efficient and chemoselective thioacetalization of carbonyl functions, transthioacetalization of O,O- and S,O-acetals and acylals [J].
Firouzabadi, H ;
Iranpoor, N ;
Hazarkhani, H .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22) :7527-7529