Three-Component Reaction of Propargyl Amines, Sulfonyl Azides, and Alkynes: One-Pot Synthesis of Tetrasubstituted Imidazoles

被引:96
作者
Jiang, Zheng [1 ]
Lu, Ping [1 ]
Wang, Yanguang [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
关键词
FACILE ACCESS; MULTICOMPONENT REACTIONS; OXIDATIVE AROMATIZATION; AZEPINE DERIVATIVES; EFFICIENT SYNTHESIS; CASCADE REACTIONS; AMIDE SYNTHESIS; RING CLOSURES; CYCLOISOMERIZATION; HYDROAMINATION;
D O I
10.1021/ol303023y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and straightforward strategy for the synthesis of tetrasubstituted imidazoles from propargyl amines, sulfonyl azides, and terminal alkynes is described. N-Sulfonyl ketenimine and aminoallene are believed to be the key intermediates for this two-step one-pot transformation.
引用
收藏
页码:6266 / 6269
页数:4
相关论文
共 71 条
[1]   Preparation of 2,5-disubstituted oxazoles from N-propargylamides [J].
Arcadi, A ;
Cacchi, S ;
Cascia, L ;
Fabrizi, G ;
Marinelli, F .
ORGANIC LETTERS, 2001, 3 (16) :2501-2504
[2]   Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction [J].
Aschwanden, P ;
Frantz, DE ;
Carreira, EM .
ORGANIC LETTERS, 2000, 2 (15) :2331-2333
[3]   Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine [J].
Bae, I ;
Han, H ;
Chang, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2038-2039
[4]   One-pot nitro-Mannich/hydroamination cascades for the direct synthesis of 2,5-disubstituted pyrroles using base and gold catalysis [J].
Barber, David M. ;
Sanganee, Hitesh ;
Dixon, Darren J. .
CHEMICAL COMMUNICATIONS, 2011, 47 (15) :4379-4381
[5]   Synthesis of fused imidazo-pyridine and -azepine derivatives by sequential van Leusen/Heck reactions [J].
Beebe, X ;
Gracias, V ;
Djuric, SW .
TETRAHEDRON LETTERS, 2006, 47 (19) :3225-3228
[6]  
Bhatnagar A., 2011, International Journal of PharmTech Research, V3, P268
[7]   Imidazole and benzimidazole derivatives as chemotherapeutic agents [J].
Boiani, M ;
González, M .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2005, 5 (04) :409-424
[8]   Reactive Silver and Cobalt Nanoparticles Modified with Fatty Acid Ligands Functionalized by Imidazole Derivatives [J].
Bromberg, Lev ;
Chen, Liang ;
Chang, Emily P. ;
Wang, Sa ;
Hatton, T. Alan .
CHEMISTRY OF MATERIALS, 2010, 22 (18) :5383-5391
[9]   Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides [J].
Cassidy, Michael P. ;
Raushel, Jessica ;
Fokin, Valery V. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3154-3157
[10]   Active-site structure analysis of recombinant human inducible nitric oxide synthase using imidazole [J].
Chabin, RM ;
McCauley, E ;
Calaycay, JR ;
Kelly, TM ;
MacNaul, KL ;
Wolfe, GC ;
Hutchinson, NI ;
Madhusudanaraju, S ;
Schmidt, JA ;
Kozarich, JW ;
Wong, KK .
BIOCHEMISTRY, 1996, 35 (29) :9567-9575