SciELO - Scientific Electronic Library Online

 
vol.19 issue3Application of Haar and Mexican hat wavelets to double divisor-ratio spectra for the multicomponent determination of ascorbic acid, acetylsalicylic acid and paracetamol in effervescent tabletsNovel lipid constituents identified in seeds of Nigella sativa (Linn) author indexsubject indexarticles search
Home Pagealphabetic serial listing  

Services on Demand

Journal

Article

Indicators

Related links

Share


Journal of the Brazilian Chemical Society

Print version ISSN 0103-5053On-line version ISSN 1678-4790

Abstract

BOECHAT, Núbia et al. N-Acyl-3,3-difluoro-2-oxoindoles as versatile intermediates for the preparation of different 2,2-difluorophenylacetic derivatives. J. Braz. Chem. Soc. [online]. 2008, vol.19, n.3, pp.445-457. ISSN 1678-4790.  https://doi.org/10.1590/S0103-50532008000300011.

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.

Keywords : isatins; DAST; deoxo-fluor; 1,3,4-thiadiazoles; 3,3-difluoro-2-oxoindoles; N-acyl-3,3-difluoro-2-oxoindoles.

        · abstract in Portuguese     · text in English     · English ( pdf )

 

Creative Commons License All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License