Efficient room-temperature synthesis of tri- and tetrasubstituted imidazoles catalyzed by ZrCl4

被引:173
作者
Sharma, G. V. M. [1 ]
Jyothi, Y. [1 ]
Lakshmi, P. Sree [1 ]
机构
[1] Indian Inst Chem Technol, Chem Div 3, Div Organ Chem 3, Discovery Lab, Hyderabad 500007, Andhra Pradesh, India
关键词
1,2-diarylethanedienones; imidazole glycoconjugates; three/four-component coupling reaction; tri/tetrasubstituted imidazoles;
D O I
10.1080/00397910600773825
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general protocol has been developed for the rapid synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles in high yields using ZrCl4 as an efficient catalyst at room temperature. A variety of aromatic, aliphatic, and terpenoidal aldehydes underwent condensation with NH4OAc/amines to give the imidazoles. Similarly, the imidazole glycoconjugates are prepared in good yields from the corresponding glycosyl aldehydes.
引用
收藏
页码:2991 / 3000
页数:10
相关论文
共 27 条
[1]   AN ORALLY BIOAVAILABLE HIV-1 PROTEASE INHIBITOR CONTAINING AN IMIDAZOLE-DERIVED PEPTIDE-BOND REPLACEMENT - CRYSTALLOGRAPHIC AND PHARMACOKINETIC ANALYSIS [J].
ABDELMEGUID, SS ;
METCALF, BW ;
CARR, TJ ;
DEMARSH, P ;
DESJARLAIS, RL ;
FISHER, S ;
GREEN, DW ;
IVANOFF, L ;
LAMBERT, DM ;
MURTHY, KHM ;
PETTEWAY, SR ;
PITTS, WJ ;
TOMASZEK, TA ;
WINBORNE, E ;
ZHAO, BG ;
DREYER, GB ;
MEEK, TD .
BIOCHEMISTRY, 1994, 33 (39) :11671-11677
[2]   METAL-CARBONYL CATALYSIS OF ORGANOBORANE REACTIONS - COBALT CARBONYL CATALYZED REDUCTIVE CARBONYLATION OF SCHIFF-BASES [J].
ALPER, H ;
AMARATUNGA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (18) :3593-3595
[3]   SYNTHESIS OF OXAZOLO-PHANES AND IMIDAZOLO-PHANES [J].
BECCALLI, EM ;
MAJORI, L ;
MARCHESINI, A ;
TORRICELLI, C .
CHEMISTRY LETTERS, 1980, (06) :659-662
[4]  
Brodgen RN, 1978, DRUGS, V15, P93
[5]   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
[6]  
GANELLIN CR, 1985, MED CHEM ROLE ORGANI, P93
[7]   UNTERSUCHUNGEN IN DER AZOLREIHE .5. UMSETZUNGEN DER OXAZOLONE-(2) MIT METALLORGANISCHEN VERBINDUNGEN [J].
GOMPPER, R .
CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (03) :374-382
[8]  
Grimment M. R., 1984, COMPREHENSIVE HETERO, V5, P457
[9]  
Grimmett M.R., 1996, Comprehensive Heterocyclic Chemistry, P77
[10]   D-N-[(1-BENZYL-1H-IMIDAZOL-5-YL)-ALKYL] AND L-N-[(1-BENZYL-1H-IMIDAZOL-5-YL)-ALKYL] ACIDS AS ANGIOTENSIN-II AT-1 ANTAGONISTS [J].
HILL, DT ;
GIRARD, GR ;
WEINSTOCK, J ;
EDWARDS, RM ;
WEIDLEY, EF ;
OHLSTEIN, E ;
PEISHOFF, CE ;
BAKER, E ;
AIYAR, N .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (01) :19-24