Synthesis of functionalised pyrido[4,3-b][1,4]oxazine and imidazo[1,2-a]pyridine derivatives

被引：31

作者：

Arrault, A

Touzeau, F

Guillaumet, G

Léger, JM

Jarry, C

Mérour, JY

机构：

[1] Univ Orleans, CNRS, UMR 6005, Inst Chim Organ & Analyt, F-45067 Orleans 2, France

[2] Univ Bordeaux 2, EA Pharmacochim, Chim Phys & Cristallog Lab, F-33076 Bordeaux, France

来源：

TETRAHEDRON | 2002年 / 58卷 / 40期

关键词：

pyridine; cyclisation; oxazine; oxazinone;

D O I：

10.1016/S0040-4020(02)00875-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ethyl 3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-2-carboxylate derivatives were obtained from 3-hydroxy-2-aminopyridine and ethyl 2,3-dibromopropanoate. Reduction of thiolactam 17 obtained from the lactam 9 gave the corresponding ethyl 2H-pyrido[3,2b][1,4]oxazine-2-carboxylate. The use of ethyl 2-chloro-3-oxopropanoate with 2-amino-3-hydroxypyridine or 3-amino-4-hydroxypyridine led, respectively, to imidazo[1,2-a]pyridine derivatives or ethyl pyrido[4,3-b][1,4] oxazine-2-carboxylate. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：8145 / 8152

页数：8

共 53 条

[1]

Attanasi OA, 2001, HELV CHIM ACTA, V84, P2379, DOI 10.1002/1522-2675(20010815)84:8<2379::AID-HLCA2379>3.0.CO

[2]

2-5

[3] SYNTHESIS OF PHENYL-SUBSTITUTED 2H-3,4-DIHYDRO-3-AMINOMETHYL-1,4-BENZOXAZINES - INTERMEDIATES FOR 1H-2,3,3A,4-TETRAHYDROIMIDAZO-[5,1-C][1,4]BENZOXAZIN-1-ONE DERIVATIVES .2. [J].