Synthesis of fused bicyclic imidazoles by sequential van Leusen/ring-closing metathesis reactions

被引:83
作者
Gracias, V [1 ]
Gasiecki, AF [1 ]
Djuric, SW [1 ]
机构
[1] Abbott Labs, Sacffold Oriented Synth, Med Chem Technol, Abbott Pk, IL 60064 USA
关键词
D O I
10.1021/ol050852+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy employing the van Leusen three-component reaction and the ring-closing metathesis reaction in a sequential fashion to access fused bicyclic imidazole rings is reported. The two-step sequence generated compounds of significant molecular complexity from simple starting materials in an expedient fashion with excellent yields.
引用
收藏
页码:3183 / 3186
页数:4
相关论文
共 49 条
[1]   A versatile synthesis of fused triazolo derivatives by sequential Ugi/alkyne-azide cycloaddition reactions [J].
Akritopoulou-Zanze, I ;
Gracias, V ;
Djuric, SW .
TETRAHEDRON LETTERS, 2004, 45 (46) :8439-8441
[2]   Synthesis of novel fused isoxazoles and isoxazolines by sequential Ugi/INOC reactions [J].
Akritopoulou-Zanze, I ;
Gracias, V ;
Moore, JD ;
Djuric, SW .
TETRAHEDRON LETTERS, 2004, 45 (17) :3421-3423
[3]   Oxidative radical cyclisations onto imidazoles and pyrroles using Bu3SnH [J].
Aldabbagh, F ;
Bowman, WR ;
Mann, E .
TETRAHEDRON LETTERS, 1997, 38 (45) :7937-7940
[4]   Synthesis and structure -: Activity relationship of a new series of COX-2 selective inhibitors:: 1,5-diarylimidazoles [J].
Almansa, C ;
Alfón, J ;
de Arriba, AF ;
Cavalcanti, FL ;
Escamilla, I ;
Gómez, LA ;
Miralles, A ;
Soliva, R ;
Bartrolí, J ;
Carceller, E ;
Merlos, M ;
García-Rafanell, J .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (16) :3463-3475
[5]   Application of tandem Ugi reaction/ring-closing metathesis in multicomponent synthesis of unsaturated nine-membered lactams [J].
Banfi, L ;
Basso, A ;
Guanti, G ;
Riva, R .
TETRAHEDRON LETTERS, 2003, 44 (41) :7655-7658
[6]   Short and diverse route toward complex natural product-like macrocycles [J].
Beck, B ;
Larbig, G ;
Mejat, B ;
Magnin-Lachaux, M ;
Picard, A ;
Herdtweck, E ;
Dömling, A .
ORGANIC LETTERS, 2003, 5 (07) :1047-1050
[7]   Highly substituted pyrrolidinones and pyridones by 4-CR/2-CR sequence [J].
Beck, B ;
Picard, A ;
Herdtweck, E ;
Dömling, A .
ORGANIC LETTERS, 2004, 6 (01) :39-42
[8]   FADROZOLE HYDROCHLORIDE - A POTENT, SELECTIVE, NONSTEROIDAL INHIBITOR OF AROMATASE FOR THE TREATMENT OF ESTROGEN-DEPENDENT DISEASE [J].
BROWNE, LJ ;
GUDE, C ;
RODRIGUEZ, H ;
STEELE, RE ;
BHATNAGER, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :725-736
[9]   Synthesis of fused bicyclic imidazoles by ring-closing metathesis [J].
Chen, YZ ;
Dias, HVR ;
Lovely, CJ .
TETRAHEDRON LETTERS, 2003, 44 (07) :1379-1382
[10]   An asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of oxygen heterocycles: An efficient approach to the enantioselective synthesis of (+)-laurencin [J].
Crimmins, MT ;
Choy, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) :5653-5660