Cu-Catalyzed Three-Component Cascade Synthesis of 1,3-Benzothiazines from ortho-Aminohydrazones and Bromodifluoroacetamides

被引：9

作者：

Yu, Changjiang ^{[1
,2
]}

Ke, Fumei ^{[1
,2
]}

Su, Jianke ^{[1
,2
]}

Ma, Xingxing ^{[3
]}

Li, Xin ^{[1
,2
]}

Song, Qiuling ^{[1
,2
,3
,4
,5
,6
]}

机构：

[1] Huaqiao Univ, Inst Next Generat Matter Transformat, Coll Chem Engn, Xiamen 361021, Fujian, Peoples R China

[2] Huaqiao Univ, Coll Mat Sci Engn, Xiamen 361021, Fujian, Peoples R China

[3] Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Fujian, Peoples R China

[4] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[5] Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

[6] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 42期

基金：

中国国家自然科学基金;

关键词：

EFFICIENT SYNTHESIS; DIFLUOROMETHYLATION; CHLORODIFLUOROMETHANE; ACCESS;

D O I：

10.1021/acs.orglett.2c03399

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and convenient synthesis of benzo[d][1,3]thiazine has been developed by employing a copper-catalyzed transformation of readily available ketone-derived hydrazones with elemental sulfur and bromodifluoroalkylative reagents. The strategy involves an S-8-catalyzed selective triple-cleavage of bromodifluoroacetamides, which acts as a C1 synthon at the 2-position of benzo[d][1,3]thiazine. A mechanism proceeding through a Cu-carbene intermediate is proposed for the C-S bond formation.

引用

页码：7861 / 7865

页数：5

共 46 条

[1] Synthesis of 2,4-difuryl-4H-3,1-benzothiazines via a furan ring migration reaction [J].