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

Bastos, Mônica M.¹  Silva, Filipe S. Q. da¹  Wardell, Solange M. S. V.¹  Mendonça, Jorge S.¹  Mayer, Lúcia M. U.¹  Arruda, Monique S. L.¹  Sá, Paula M.¹  Fundação Oswaldo Cruz, Rio de Janeiro, Brazil¹  Kover, Warner B.¹  Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil¹  Maciel, Lindalva C.¹  Boechat, Núbia¹  Pinto, Angelo C.¹ 

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

学科分类：化学（综合）

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.

【 授权许可】

Unknown