Aminoimidazo[1,2-a]pyridines:: regioselective synthesis of substituted imidazonaphthyridines, azacarbolines and cyclazines

被引：21

作者：

Chezal, JM

Moreau, E

Chavignon, O

Gaumet, V

Métin, J

Blache, Y

Diez, A

Fradera, X

Luque, J

Teulade, JC

机构：

[1] INSERM, UMR 484, Fac Pharm, F-63001 Clermont Ferrand 1, France

[2] Fac Pharm Montpellier, Lab Chim Organ Pharmaceut, EA 2414, F-34060 Montpellier, France

[3] Univ Barcelona, Fac Farm, Lab Quim Organ, E-08028 Barcelona, Spain

[4] Univ Barcelona, Fac Farm, Dept Fisicoquim, E-08028 Barcelona, Spain

来源：

TETRAHEDRON | 2002年 / 58卷 / 02期

关键词：

imidazo[1,2-a]pyridine; imidazonaphthyridine; azacarboline; cyclazine;

D O I：

10.1016/S0040-4020(01)01141-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In order to study the regioselectivity of thermal cyclocondensation, aminoimidazo [1,2-a]pyridines (AIP) 5a-e were prepared, further converted into iminophosphoranes 7a-e, and ultimately converted regioselectively in angular annulated imidazonaphthyridines (IN) 8a, 10a, 11a, 12a or linear annulated dipyridoimidazole (DPI) 17a. From 2-substituted derivative 23, the peri annulated product 24a was obtained. The starting amines 5a-f reacted with aldehydes to yield regioselectively IN 8a-c, 10a-c, 11a-c, 12a,b, DPI 16a-e, 17a-d and TIBO like structures (+/-)-13 and 24a-c, as proved by X-ray analysis. The 1,2- or 1,4-addition between amines and alpha,beta-unsaturated aldehydes concerning the pyridine and imidazole moieties is discussed in the light of these results. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：295 / 307

页数：13

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