A novel multicomponent synthesis of polysubstituted 5-aminooxazole and its new scaffold-generating reaction to pyrrolo[3,4-b]pyridine

被引:159
作者
Sun, XW
Janvier, P
Zhao, G
Bienaymé, H
Zhu, JP [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
[2] Rhone Poulenc, F-69153 Decines Charpieu, France
关键词
D O I
10.1021/ol007055q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A novel three-component synthesis of 5-amino oxazole (1) is reported. Its subsequent reaction with ag unsaturated acyl chloride leads to polysubstituted pyrrolopyridine (2), A triple domino process, acylation/IMDA/retro-Michael cycloreversion, was involved in the latter process. The methodology allows the quick preparation, from simple and readily available inputs, of highly functionalized title compounds not easily accessed by other methods.
引用
收藏
页码:877 / 880
页数:4
相关论文
共 78 条
[1]   Molecular basis of peripheral vs central benzodiazepine receptor selectivity in a new class of peripheral benzodiazepine receptor ligands related to alpidem [J].
Anzini, M ;
Cappelli, A ;
Vomero, S ;
Giorgi, G ;
Langer, T ;
Bruni, G ;
Romeo, MR ;
Basile, AS .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (21) :4275-4284
[2]   Multiple-component condensation strategies for combinatorial library synthesis [J].
Armstrong, RW ;
Combs, AP ;
Tempest, PA ;
Brown, SD ;
Keating, TA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131
[3]  
Bhandari A, 1999, SYNTHESIS-STUTTGART, P1951
[4]   Synthesis of rigid hydrophobic tetrazoles using an Ugi multi-component heterocyclic condensation [J].
Bienaymé, H ;
Bouzid, K .
TETRAHEDRON LETTERS, 1998, 39 (18) :2735-2738
[5]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[6]  
2-A
[7]  
BOGDANOV VS, 1980, IAN SSSR KH, P1017
[8]  
BOSSIO R, 1991, LIEBIGS ANN CHEM, P1107
[9]  
BOSSIO R, 1989, HETEROCYCLES, V29, P1829
[10]   RECENT ADVANCES IN THE USE OF TANDEM REACTIONS FOR ORGANIC-SYNTHESIS [J].
BUNCE, RA .
TETRAHEDRON, 1995, 51 (48) :13103-13159