I-2-DMSO Promoted Deaminative Coupling Reactions of Glycine Esters: Access to 5-(Methylthio)pyridazin-3(2H)-ones

An unprecedented, one-step strategy for the synthesis of 5-(methylthio)pyridazin-3(2H)-one derivatives has been developed through iodine triggered deaminative coupling of glycine esters with methyl ketones and hydrazine hydrate in DMSO. These transformations in the absence of hydrazine helped to generate different 3-methylthio-4-oxo-enoates in good yields. Notably, DMSO played multiple roles such as oxidant, methylthiolating reagent, and solvent.

Automated summary

An unprecedented one-step strategy for synthesizing 5-(methylthio)pyridazin-3(2H)-one derivatives has been developed through iodine triggered deaminative coupling. This strategy involves the reaction of glycine esters with methyl ketones and hydrazine hydrate in DMSO. The transformations, in the absence of hydrazine, generated various 3-methylthio-4-oxo-enoates in good yields. Notably, DMSO played multiple roles as an oxidant, methylthiolating reagent, and solvent.