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

Showkat Ahmad Bhat, Mohammad Yaqoob Bhat, Suhail Ahmad Rather, Salman Jameel, Khursheed Ahmad Bhat, Qazi Naveed Ahmed

2023Organic Letters12 citationsDOI

Abstract

An unprecedented, one-step strategy for the synthesis of 5-(methylthio)pyridazin-3(2 H )-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.

Topics & Concepts

ChemistryHydrazine (antidepressant)ReagentHydrateGlycineSolventOrganic chemistryCombinatorial chemistryCoupling (piping)Amino acidEngineeringMechanical engineeringChromatographyBiochemistryPhenothiazines and Benzothiazines Synthesis and ActivitiesCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
I<sub>2</sub>-DMSO Promoted Deaminative Coupling Reactions of Glycine Esters: Access to 5-(Methylthio)pyridazin-3(2<i>H</i>)-ones | Litcius