10.1007/BF00953940
The research focuses on the development of a general method for the synthesis of substituted 4-aryl-3-cyano-2[IH]pyridinethiones and their corresponding selenones. The purpose of this study was to overcome the limitations associated with the complexity of realization and the difficult availability of starting compounds in previously known methods. The researchers achieved this by investigating the interaction of carbonyl compounds, specifically RICH2COR2 (where R1 and R2 can be H, Me, Ac, COOEt, or various alkyl chains), and their enamines with arylidene derivatives of cyanothioacetamide and cyanoselenoacetamide. The process involved the use of organic bases as catalysts and led to the formation of the desired pyridinethiones and pyridineselenones. The study concluded that this new method is sufficiently general and provides a way to synthesize these compounds with good yields. The chemicals used in the process include various arylidenethio(seleno)acetamides, carbonyl compounds, enamines, and organic bases such as piperidine, diethylamine, hexamethyleneimine, and morpholine.
10.1016/j.tetasy.2010.01.007
Vrushali H. Jadhav et al. describe a method for synthesizing azepane and nojirimycin iminosugars using the Sharpless asymmetric epoxidation of D-glucose-derived allyl alcohol. The researchers achieved high stereoselectivity in the formation of a- and ?-epoxides, which were then selectively opened with sodium azide to predominantly form 6-azido diols over 5-azido diols. These azido diols were subsequently converted into the corresponding seven-membered azepane and six-membered nojirimycin iminosugars. The study highlights the importance of these iminosugars as glycosidase inhibitors with potential applications in treating diseases like diabetes, cancer, and viral infections. The authors also discuss the challenges and ongoing efforts to improve the regioselectivity of the epoxide ring opening to favor the formation of 5-azido diols, which could further enhance the synthesis of these bioactive compounds.