Multicomponent domino process to oxa-bridged polyheterocycles and pyrrolopyridines, structural diversity derived from work-up procedure

被引：60

作者：

Gámez-Montaño, R ^{[1
]}

González-Zamora, E ^{[1
]}

Potier, P ^{[1
]}

Zhu, JP ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

TETRAHEDRON | 2002年 / 58卷 / 32期

关键词：

multi-component reaction; isonitrile; polyheterocycle; pyrrolopyridine; high throughput synthesis;

D O I：

10.1016/S0040-4020(02)00634-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel three-component domino processes to polyheterocycles are developed. Reaction of an allylamine (3), an aldehyde (4) and an alpha-isocyanoacetamide (5) in methanol at room temperature provides an efficient access to oxa-bridged tricycle (1) as a single diastereoisomer. In this one-pot process, one C-N, one C-O and three C-C bonds are formed with concomitant creation of five asymmetric centers. While isolable, the oxa-bridged tricycles (1) can be cleanly in-situ fragmented to pyrrolopyridines (2) under acidic conditions (trifluoroacetic acid, -78degreesC), providing thus an unusual work-up derived structural diversity. The operational simplicity and excellent chemical yield make these novel heterocycle syntheses valuable in diversity-oriented high throughput synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：6351 / 6358

页数：8

共 62 条

[1] Molecular basis of peripheral vs central benzodiazepine receptor selectivity in a new class of peripheral benzodiazepine receptor ligands related to alpidem
Anzini, M
Cappelli, A
Vomero, S
Giorgi, G
Langer, T
Bruni, G
Romeo, MR
Basile, AS
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (21) : 4275 - 4284
[2] Multiple-component condensation strategies for combinatorial library synthesis
Armstrong, RW
Combs, AP
Tempest, PA
Brown, SD
Keating, TA
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) : 123 - 131
[3] Arya P, 2001, ANGEW CHEM INT EDIT, V40, P339, DOI 10.1002/1521-3773(20010119)40:2<339::AID-ANIE339>3.0.CO
[4] 2-J
[5] Bhandari A, 1999, SYNTHESIS-STUTTGART, P1951
[6] Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[7] 2-A
[8] BOGDANOV VS, 1980, IAN SSSR KH, P1017
[9] RECENT ADVANCES IN THE USE OF TANDEM REACTIONS FOR ORGANIC-SYNTHESIS
BUNCE, RA
[J]. TETRAHEDRON, 1995, 51 (48) : 13103 - 13159
[10] SYNTHESIS OF TRICYCLIC AMINOPYRIDINES BY A CADMIUM PROMOTED CYCLIZATION
CAMPBELL, JB
FIROR, JW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (16) : 5243 - 5249

← 1 2 3 4 5 6 7 →