Direct and safe one-pot synthesis of functionalized dimethyl 1-aryl-1,9a-dihydropyrido[2,1-c][1,4]thiazine-1-phosphonates

被引：7
|
作者：
Wei, Yuliang [1 ]
Sun, Simin [1 ]
Xu, Jiaxi [1 ]
机构：
[1] Beijing Univ Chem Technol, Fac Sci, Dept Organ Chem, State Key Lab Chem Resource Engn, Beijing 100029, Peoples R China
来源：
TETRAHEDRON LETTERS | 2023年 / 120卷
基金：
中国国家自然科学基金;
关键词：
One -pot synthesis; Phosphonate; Pyrido[2; c ][1; 4]thiazine; 4-Thiazine; Visible -light -induced reaction;
D O I：
10.1016/j.tetlet.2023.154444
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A visible-light-induced direct and safe synthesis of functionalized dimethyl 1-aryl-1,9a-dihydropyrido [2,1-c][1,4]thiazine-1-phosphonates is realized from dimethyl (aryl(2-tosylhydrazono)methyl)phosphonates and pyridinium 1,4-zwitterionic thiolates with cesium carbonate as base in dichloromethane. The reaction involves the carbene generation from dimethyl (aryl(2-tosylhydrazono)methyl)phosphonates in the presence of cesium carbonate as base and the [1+5] annulation of the carbenes with pyridinium 1,4-zwitterionic thiolates to synthesize functionalized 1,9a-dihydropyrido[2,1-c][1,4]thiazine derivatives. The method avoids preparing, storing, and using potentially dangerous phosphoryl diazo compounds and features simple, convenient, catalyst-free, and mild reaction conditions.(c) 2023 Elsevier Ltd. All rights reserved.
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页数：4
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