N-Acyl-3,3-difluoro-2-oxoindoles as versatile intermediates for the preparation of different 2,2-difluorophenylacetic derivatives

Journal of the Brazilian Chemical Society

Núbia Boechat²  Warner B. Kover¹  Mônica M. Bastos²  Angelo C. Pinto¹  Lindalva C. Maciel²  Lúcia M. U. Mayer²  Filipe S. Q. Da Silva²  Paula M. Sá²  Jorge S. Mendonça²  Solange M. S. V. Wardell²  Monique S. L. Arruda² 

[1] ,Fundação Oswaldo Cruz Far-Manguinhos Rio de Janeiro RJ ,Brazil

关键词: isatins;    DAST;    deoxo-fluor;    1;    3;    4-thiadiazoles;    3;    3-difluoro-2-oxoindoles;    N-acyl-3;    3-difluoro-2-oxoindoles;   

DOI  :  10.1590/S0103-50532008000300011

来源: SciELO

【 摘 要 】

This paper describes the versatility of N-Acyl-3,3-difluoro-2-oxoindoles, obtained from the the reaction of N-acylisatins with (diethylamino)sulphur trifluoride (DAST) which, on opening of the heterocyclic ring by reactions with nucleophiles, lead to the formation of a variety of products: reaction with water yields 2-(2-amidoacyl)-2,2-difluoroacetic acids, with alcohols yields alkyl 2-(2-amidoacyl)-2,2-difluoroacetates, with amines and glycine yields 2-(2-amidoacyl)-2,2-difluoroacetamides and with thiosemicarbazides yields difluorothiosemicarbazide derivatives. The latter undergo acid-catalysed cyclizations to yield N-(2-((5-aminoaryl-1,3,4-thiadiazol-2-yl)difluoromethyl)-4-(R)-phenyl)acetamide. The X-ray structure of N-(2-((5-amino-1,3,4-thiadiazol-2-yl)difluoromethyl)-4-methylphenyl)acetamide has been determined.

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