A mild and efficient one-pot synthesis of 2-dihydroimidazoles from aldehydes

被引:123
作者
Fujioka, H [1 ]
Murai, K [1 ]
Ohba, Y [1 ]
Hiramatsu, A [1 ]
Kita, Y [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
关键词
dihydroimidazole; aldehyde; 1,2-diamine; N; N-Acetal; N-halosuccinimide; mild reaction;
D O I
10.1016/j.tetlet.2005.02.025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reactions of various aldehydes and 1,2-diamines followed by NXS treatment proceed at 0 degrees C to give the corresponding dihydroimidazoles in high yields. The reaction is mild, and many functional groups such as halogens, nitrites, and esters can exist. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2197 / 2199
页数:3
相关论文
共 24 条
[1]   Synthesis and pharmacological evaluation of imidazoline sites I1 and I2 selective ligands [J].
Anastassiadou, M ;
Danoun, S ;
Crane, L ;
Baziard-Mouysset, G ;
Payard, M ;
Caignard, DH ;
Rettori, MC ;
Renard, P .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (03) :585-592
[2]   ASYMMETRIC CATALYSIS .46. ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH [RH(COD)CL]2 AND OPTICALLY-ACTIVE NITROGEN LIGANDS [J].
BOTTEGHI, C ;
SCHIONATO, A ;
CHELUCCI, G ;
BRUNNER, H ;
KURZINGER, A ;
OBERMANN, U .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 370 (1-3) :17-31
[3]   1-BENZAZEPINE DERIVATIVES ACTING AS ATP-DEPENDENT POTASSIUM CHANNELS ANTAGONISTS [J].
CORBEL, JC ;
URIAC, P ;
HUET, J ;
MARTIN, CAE ;
ADVENIER, C .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1995, 30 (01) :3-13
[4]   Stereoselective synthesis of quaternary benzylic carbons using C2 symmetric imidazolines and tetrahydrofuran as electrophile [J].
Dalko, PI ;
Langlois, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8107-8117
[5]   Chiral pyridylimidazolines: synthesis, arene ruthenium complexes and application in asymmetric catalysis [J].
Davenport, AJ ;
Davies, DL ;
Fawcett, J ;
Russell, DR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (13) :1500-1503
[6]   THE CHEMISTRY OF THE 2-IMIDAZOLINES AND IMIDAZOLIDINES [J].
FERM, RJ ;
RIEBSOMER, JL .
CHEMICAL REVIEWS, 1954, 54 (04) :593-613
[7]  
Gilman A. G., 2001, PHARM BASIC THERAPEU
[8]  
GREENHILL JV, 1993, PROGR MEDICINAL CHEM, V3
[9]  
Grimmett M.R., 1996, Comprehensive Heterocyclic Chemistry, P77
[10]   A novel synthetic method for 2-arylmethyl substituted imidazolines and imidazoles from 2-aryl-1,1-dibromoethenes [J].
Huh, DH ;
Ryu, H ;
Kim, YG .
TETRAHEDRON, 2004, 60 (44) :9857-9862