1342864-93-0Relevant academic research and scientific papers
Divergent Synthesis of Disulfanes and Benzenesulfonothioates Bearing 2-Aminofurans From N-Tosylhydrazone-Bearing Thiocarbamates
Mai, Shaoyu,Song, Qiuling
supporting information, p. 7952 - 7957 (2017/06/27)
An efficient and convenient synthesis of valuable disulfanes and benzenesulfonothioates, having a 2-aminofuran framework, has been developed by employing a copper-catalyzed transformation of readily available N-tosylhydrazone-bearing thiocarbamates. This method features an inexpensive metal catalyst, mild reaction conditions, good functional-group tolerance, short reaction times, and delivers valuable and complex products. A copper carbene generated from an N-tosylhydrazone-bearing thiocarbamate is proposed as the key intermediate for the transformation and it triggers the subsequent cascade. Remarkably, the Ts anion released from N-tosylhydrazone further serves as a nucleophile, thus rendering the formation of benzenesulfonothioates under controlled conditions.
Effective synthesis of ortho-substituted trithiophenol amines by Miyazaki-Newman-Kwart rearrangement
Gjoka, Blerina,Romano, Francesco,Zonta, Cristiano,Licini, Giulia
experimental part, p. 5636 - 5640 (2011/11/29)
An efficient synthesis of ortho-substituted trithiophenol amines from commercially available salicaldehydes by Miyazaki-Newman-Kwart rearrangement/threefold reductive amination is reported. The rearrangement has been carried out on salicaldehyde-O-thiocarbamates using microwave induced heating, which furnishes a series of thiosalicaldehyde-S-carbamates in high yield. The thiocarbamate has three roles: it enables effective S-O rearrangement, acts as a protecting group during the threefold reductive amination and can be easily removed under reductive conditions. The three-step synthesis has an overall yield ranging from 30-35 %, and it enables access to a series of increasingly important C3v symmetric ligands in a structurally systematic way.
