Phenol Ugi-smiles systems:: strategies for the multicomponent N-arylation of primary amines with isocyanides, aldehydes, and phenols

被引:154
作者
El Kaïm, L [1 ]
Grimaud, L [1 ]
Oble, J [1 ]
机构
[1] Ecole Natl Super Tech Avancees, CNRS, UMR 7652, Chim Organ Lab, F-75015 Paris, France
关键词
amines; arylation; multicomponent reaction; phenols; rearrangement;
D O I
10.1002/anie.200502636
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A Smiles rearrangement is the key step in the efficient coupling of primary amines with isocyanides, carbonyl compounds, and electron-deficient substituted phenols to form N-aryl amines (see picture). The presence of a nitro or ester group on the resulting adduct allows applications in heterocyclic synthesis. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7961 / 7964
页数:4
相关论文
共 30 条
[1]  
Banfi L., 2005, ORG REACTIONS, V65, P1, DOI [10.1002/0471264180.or065.01, DOI 10.1002/0471264180.0R065.01]
[2]  
Bienaymé H, 1998, ANGEW CHEM INT EDIT, V37, P2234, DOI 10.1002/(SICI)1521-3773(19980904)37:16<2234::AID-ANIE2234>3.0.CO
[3]  
2-R
[4]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[5]  
2-A
[6]  
Bienayme H., 1998, ANGEW CHEM, V110, P2349, DOI DOI 10.1002/(SICI)1521-3757(19980817)110:16
[7]   Parallel synthesis of 3-aminoimidazo[1,2-a]pyridines and pyrazines by a new three-component condensation [J].
Blackburn, C ;
Guan, B ;
Fleming, P ;
Shiosaki, K ;
Tsai, S .
TETRAHEDRON LETTERS, 1998, 39 (22) :3635-3638
[8]   AROMATIC NUCLEOPHILIC SUBSTITUTION REACTIONS [J].
BUNNETT, JF ;
ZAHLER, RE .
CHEMICAL REVIEWS, 1951, 49 (02) :273-412
[9]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[10]  
2-U