Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

被引：2

作者：

Vinogradov, Dmitry B. ^{[1
]}

Izmest'ev, Alexei N. ^{[1
]}

Kravchenko, Angelina N. ^{[1
]}

Strelenko, Yuri A. ^{[1
]}

Gazieva, Galina A. ^{[1
]}

机构：

[1] Russian Acad Sci, N D Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 19卷

关键词：

N; S-heterocycles; ring expansion; skeletal rearrangement; 1; 3-thiazines; thiazolidine-4-ones; HEPATITIS-C VIRUS; DERIVATIVES;

D O I：

10.3762/bjoc.19.80

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines was synthesized via a cascade sequence of hydrolysis and skeletal re-arrangement of imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazin-7(8H)-ylidene)acetic acid esters in methanol upon treatment with excess KOH. Imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazin-6(7H)-ylidene)acetic acid esters are also suitable substrates for the reaction. In this case hydrolysis and thiazole ring expansion were accompanied with the change of the thiazolotriazine junction type from thia-zolo[3,2-b][1,2,4]triazine to thiazino[2,3-c][1,2,4]triazine.

引用

页码：1047 / 1054

页数：8

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