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：4
|
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
收藏
页码：1047 / 1054
页数：8
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