I2-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 gen...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 14; pp. 2382 - 2387
Main Authors Bhat, Showkat Ahmad, Bhat, Mohammad Yaqoob, Rather, Suhail Ahmad, Jameel, Salman, Bhat, Khursheed Ahmad, Ahmed, Qazi Naveed
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 14.04.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHEMISTRY
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00306