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

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.

Bibliographic Details

Main Authors:	Boechat,Núbia, Kover,Warner B., Bastos,Mônica M., Pinto,Angelo C., Maciel,Lindalva C., Mayer,Lúcia M. U., Silva,Filipe S. Q. da, Sá,Paula M., Mendonça,Jorge S., Wardell,Solange M. S. V., Arruda,Monique S. L.
Format:	Digital revista
Language:	English
Published:	Sociedade Brasileira de Química 2008
Online Access:	http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000300011
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