Direct access to heterocyclic scaffolds by new multicomponent Ugi-smiles couplings

被引:66
作者
El Kaim, Laurent [1 ]
Gizolme, Marie [1 ]
Grimaud, Laurence [1 ]
Oble, Julie [1 ]
机构
[1] Ecole Normale Super Tech Avancees, Lab Chim & Proc, F-75739 Paris 15, France
关键词
D O I
10.1021/ol061605o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New heterocyclic scaffolds can be easily prepared by the coupling of heteroaromatic phenols (pyridines, pyrimidines) with carbonyl compounds, amines, and isocyanides. This transformation related to the Ugi reaction probably involves a Smiles rearrangement. The scope of this methodology is further extended by the successful use of heterocyclic thiols to form highly functionalized thioamides.
引用
收藏
页码:4019 / 4021
页数:3
相关论文
共 35 条
[1]  
Banfi L., 2005, ORG REACTIONS, V65, P1, DOI [10.1002/0471264180.or065.01, DOI 10.1002/0471264180.0R065.01]
[2]   Potential antimalarials .22. Some 2,4-diamino-5-(3- and 4-trifluoromethylphenyl and 3,4-methylenedioxyphenyl)pyrimidines [J].
Barlin, GB ;
Kotecka, B ;
Rieckmann, KH .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1996, 49 (06) :647-650
[3]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[4]  
2-A
[5]   ANIL-SYNTHESIS .23. PREPARATION OF STYRYL AND STILBENYL DERIVATIVES OF PYRIMIDINES [J].
BURDESKA, K ;
FUHRER, H ;
KABAS, G ;
SIEGRIST, AE .
HELVETICA CHIMICA ACTA, 1981, 64 (01) :113-152
[6]  
Chen H., 2005, PCT Int. Appl, Patent No. [WO 2005058315, 2005058315, 2005/058315]
[7]   A one-pot synthesis of pyrido[2,3-b][1,4]oxazin-2-ones [J].
Cho, SD ;
Park, YD ;
Kim, JJ ;
Lee, SG ;
Ma, C ;
Song, SY ;
Joo, WH ;
Falck, JR ;
Shiro, M ;
Shin, DS ;
Yoon, YJ .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7918-7920
[8]   2-aminopyridines as highly selective inducible nitric oxide synthase inhibitors. Differential binding modes dependent on nitrogen substitution [J].
Connolly, S ;
Aberg, A ;
Arvai, A ;
Beaton, HG ;
Cheshire, DR ;
Cook, AR ;
Cooper, S ;
Cox, D ;
Hamley, P ;
Mallinder, P ;
Millichip, I ;
Nicholls, DJ ;
Rosenfeld, RJ ;
St-Gallay, SA ;
Tainer, J ;
Tinker, AC ;
Wallace, AV .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (12) :3320-3323
[9]   N-aryl 2,6-dimethoxybiphenylalanine analogues as VLA-4 antagonists [J].
Doherty, GA ;
Kamenecka, T ;
McCauley, E ;
Van Riper, G ;
Mumford, RA ;
Tong, S ;
Hagmann, WK .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (05) :729-731
[10]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO