Methyl Pyruvate Oxime as a Carbonyl Synthon: Synthesis of Ureas, Carbamates, Thiocarbamates, and Anilides

A new strategy for the synthesis of unsymmetrical ureas, carbamates, thiocarbamates, and anilides was developed with methyl pyruvate oxime as the carbonyl synthon. The intrinsic reactivity of the reagent enabled consecutive disubstitution involving direct amidation and one-pot deoximative substituti...

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Bibliographic Details
Published in:Organic letters 2024-05, Vol.26 (18), p.3850-3854
Main Authors: Kim, Seo Yeon, Lim, Hee Nam
Format: Article
Language:English
Subjects:
anilides
Lewis bases
pyruvic acid
thiocarbamates
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Summary:A new strategy for the synthesis of unsymmetrical ureas, carbamates, thiocarbamates, and anilides was developed with methyl pyruvate oxime as the carbonyl synthon. The intrinsic reactivity of the reagent enabled consecutive disubstitution involving direct amidation and one-pot deoximative substitution with various nucleophiles. The utility of the method was demonstrated with the synthesis of bioactive molecules.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01007