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Direct Access to Thio- and Seleno-acetamides Bearing (Benzo)thiazoles by a Base-Promoted One-Pot Two-Step Three-Component Reaction of 2-Amino(benzo)thiazoles with Aryl Acetyl Chlorides and Dichalcogenides

Authors :
Tang, Jingjie
Xie, Luying
Liu, Jiayu
Shi, Shangyu
Yang, Qikun
Zhang, Bo
Wang, Yingying
Chen, Lin
Jia, Shaohui
Ma, Mingfang
Xie, Zengyang
Source :
The Journal of Organic Chemistry; 20240101, Issue: Preprints
Publication Year :
2024

Abstract

Highly efficient and practical carbon–chalcogen (S, Se) and amide bonds formation methodologies for the synthesis of thio- and seleno-acetamides were developed, via the base-promoted one-pot two-step reactions of 2-amino(benzo)thiazoles and aryl acetyl chlorides with dichalcogenides. This cross-coupling reaction afforded the goal products that had been chalcogenated regioselectively in moderate to good yields. Further transformations of the new synthesized compounds, DFT calculations and preliminary mechanism studies are discussed as well.

Details

Language :
English
ISSN :
00223263
Issue :
Preprints
Database :
Supplemental Index
Journal :
The Journal of Organic Chemistry
Publication Type :
Periodical
Accession number :
ejs65649839
Full Text :
https://doi.org/10.1021/acs.joc.3c02145