Synthesis of 3-(trifluoromethyl)benzo[c][1,6]naphthyridines from substituted 4H-pyran-4-ones via 4-amino-5-aryl-2-(trifluoromethyl)pyridin

被引：25

作者：

Tyvorskii, VI

Bobrov, DN

Kulinkovich, OG

Aelterman, W

De Kimpe, N

机构：

[1] Belarusian State Univ, Dept Organ Chem, Minsk 220050, BELARUS

[2] Univ Ghent, Fac Agr & Appl Biol Sci, Dept Organ Chem, B-9000 Ghent, Belgium

来源：

TETRAHEDRON | 2000年 / 56卷 / 37期

关键词：

2-(trifluoromethyl)-4H-pyran-4-ones; 3(2H)-furanones; 4-aminopyridines; benzo[c][1,6]naphthyridines; Pictet-Hubert cyclization;

D O I：

10.1016/S0040-4020(00)00637-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclization of acylated 4-amino-5-aryl-2-(trifluoromethyl)pyridines under the action of P2O5/POCl3 smoothly afforded 3-(trifluoromethyl)benzo[c][1,6]naphthyridines in good yields. Intermediate aminopyridines were synthesized in a two-step sequence from the corresponding 4H-pyran-4-ones, which were prepared by reaction of 2-acetyl-2-aryloxiranes and 4-dimethylamino-3-(4-methoxyphenyl)-3-buten-2-one with ethyl trifluoroacetate under basic conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7313 / 7318

页数：6