Synthesis of Multisubstituted Imidazoles via Copper-Catalyzed [3+2] Cycloadditions

被引:91
作者
Tang, Dong
Wu, Ping
Liu, Xiang
Chen, Yong-Xin
Guo, Shuai-Bo
Chen, Wen-Lin
Li, Jia-Gen
Chen, Bao-Hua [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
基金
美国国家科学基金会;
关键词
ONE-POT SYNTHESIS; SUBSTITUTED IMIDAZOLES; EFFICIENT; SYSTEM;
D O I
10.1021/jo302555z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple route for the synthesis of imidazole derivatives via copper-catalyzed [3+2] cycloaddition reaction is described. This strategy has achieved high regioselectivity and used oxygen as an oxidant without the addition of expensive catalysts to provide moderate to good yields.
引用
收藏
页码:2746 / 2750
页数:5
相关论文
共 33 条
[1]  
Al-Raqa S. Y., 2006, HETEROATOM CHEM, V7, P643
[2]   Ambivalent role of metal chlorides in ring opening reactions of 2H-azirines: synthesis of imidazoles, pyrroles and pyrrolinones [J].
Auricchio, Sergio ;
Truscello, Ada M. ;
Lauria, Mirvana ;
Meille, Stefano V. .
TETRAHEDRON, 2012, 68 (36) :7441-7449
[3]   Enantiopure cycloalkane fused tetrahydropyrans through domino Michael-ketalizations with organocatalysis [J].
Chandrasekhar, Srivari ;
Mallikarjun, Kundarapu ;
Pavankumarreddy, Gangireddy ;
Rao, Kakita Veeramohana ;
Jagadeesh, Bharatam .
CHEMICAL COMMUNICATIONS, 2009, (33) :4985-4987
[4]   Application of a novel [3+2] cycloaddition reaction to prepare substituted imidazoles and their use in the design of potent DFG-out allosteric B-Raf inhibitors [J].
Dietrich, Justin ;
Gokhale, Vijay ;
Wang, Xiadong ;
Hurley, Laurence H. ;
Flynn, Gary A. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (01) :292-304
[5]   Imidazole-containing diarylether and diarylsulfone inhibitors of farnesyl-protein transferase [J].
Dinsmore, CJ ;
Williams, TM ;
O'Neill, TJ ;
Liu, DM ;
Rands, E ;
Culberson, JC ;
Lobell, RB ;
Koblan, KS ;
Kohl, NE ;
Gibbs, JB ;
Oliff, AI ;
Graham, SL ;
Hartman, GD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (23) :3301-3306
[6]   A Submarine Journey: The Pyrrole-Imidazole Alkaloids [J].
Forte, Barbara ;
Malgesini, Beatrice ;
Piutti, Claudia ;
Quartieri, Francesca ;
Scolaro, Alessandra ;
Papeo, Gianluca .
MARINE DRUGS, 2009, 7 (04) :705-753
[7]   ANTI-MYCOTIC IMIDAZOLES .4. SYNTHESIS AND ANTIFUNGAL ACTIVITY OF KETOCONAZOLE, A NEW POTENT ORALLY ACTIVE BROAD-SPECTRUM ANTIFUNGAL AGENT [J].
HEERES, J ;
BACKX, LJJ ;
MOSTMANS, JH ;
VANCUTSEM, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (08) :1003-1005
[8]   Highly efficient, four component, one-pot synthesis of tetrasubstituted imidazoles using a catalytic amount of FeCl3 • 6H2O [J].
Heravi, Majid M. ;
Derikvand, Fatemeh ;
Haghighi, Masoumeh .
MONATSHEFTE FUR CHEMIE, 2008, 139 (01) :31-33
[9]   A one-pot synthesis of 1,2,4,5-tetraarylimidazoles using molecular iodine as an efficient catalyst [J].
Kidwai, Mazaahir ;
Mothsra, Poonam .
TETRAHEDRON LETTERS, 2006, 47 (29) :5029-5031
[10]   In vitro antifungal activities of luliconazole, a new topical imidazole [J].
Koga, Hiroyasu ;
Nanjoh, Yasuko ;
Makimura, Koichi ;
Tsuboi, Ryoji .
MEDICAL MYCOLOGY, 2009, 47 (06) :640-647