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Synthesis of N-aryl 2-chloroacetamides and their chemical reactivity towards various types of nucleophiles

Journal

SYNTHETIC COMMUNICATIONS
Volume 50, Issue 3, Pages 289-314

Publisher

TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2019.1692225

Keywords

2-Chloroacetamides; chloroacetyl chloride; imidazole; sulfides; thiophene

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The synthesis of various N-aryl 2-chloroacetamides has been described through chloroacetylation of the corresponding aryl amine. The chemical reactivity of N-aryl 2-chloroacetamides is attributed to the easy replacement of its chlorine atom by nucleophiles (namely; oxygen, nitrogen and/or sulfur). Furthermore, this nucleophilic substitution may accompanied by intramolecular cyclization to furnish miscellaneous heterocyclic systems as imidazole, pyrrole, thiazolidine-4-one and thiophene.

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