Synthesis of substituted 3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine as new scaffolds for potential bioactive compounds

被引：9

作者：

Henry, N

Sánchez, I

Sabatié, A

Bénéteau, V

Guillaumet, G ^{[1
]}

Pujol, MD

机构：

[1] Univ Orleans, Inst Chim Organ & Analyt, UMR 6005, F-45067 Orleans, France

[2] Univ Barcelona, Fac Farm, CSIC, Unitat Associada,Lab Quim Farmaceut, E-08028 Barcelona, Spain

来源：

TETRAHEDRON | 2006年 / 62卷 / 10期

关键词：

pyrido-oxazines; alpha-halocarbonyl compounds; protected; 2-aminopyridine;

D O I：

10.1016/j.tet.2005.11.071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compounds having different substituents on the heterocyclic framework were prepared by several methods from 2-acetamido-3-hydroxypyridine. The condensation of 2-protected-amino-3-hydroxypyridine with 2-chloroacrylonitrile or ethyl 2,3-dibromopropionate provided in several cases two isomeric pyrido-oxazines. Whereas the reaction of 2-acetamido-3-hydroxypyridine with methyl 2,3-dibromopropionate or with alpha-halocarbonyl compounds gave exclusively the 2-substituted pyrido-oxazine, in a one-step operation. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2405 / 2412

页数：8

共 29 条

[21] Palladium-catalyzed heteroannulation leading to heterocyclic structures with two heteroatoms:: A highly regio- and stereoselective synthesis of (Z)-4-Alkyl-2-alkyl(aryl)idene-3,4-dihydro-2H-1,4-benzoxazines and (Z)-3-alkyl(aryl)idene-4-tosyl-3,4-dihydro-2H-1,4-benzoxazines [J].