Síntese de derivados de glicero-carboidratos e amino-1,2,3-triazóis

Abstract

New synthetic strategies have been proposed for development of bioactive substances containing derivatives from renewable resource, such as glycerol and carbohydrate. Heterocyclic are other important class of compounds and among the most studied, 1,2,3-triazole are highlighted because of its synthetic versatility and wide range of biological application. The present work towards the synthesis of glycero-carbohydrates and new amino-triazole and naphthoquinone derivatives. 1,2,3-Triazoles (16-19) and (28-31) were prepared from N-[alkyl-azido]-phthalimides (11-14) and phenylacetylene (15) or 4-brome-1-butine (27) alkynes via 1,3-dipolar cycloaddition reaction in yields from 70 to 91%. Amine protection phthalimide group of 4-(phenyl)-N-(alkyl)-phthalimide-1,2,3-triazoles (16-19) was removed using hydrazine. Then, the amino-triazoles (20-22) obtained were reacted with 1,4-naphthoquinone (23) to afford the 1,2,3-triazole-2-amino-1,4-naphthoquinones (24-26) in yields of 88-89%. 4-(2-Azido-ethyl)-N-phthalimide-1,2,3-triazoles (32-35) were synthesized from the corresponding bromide compounds in yields of 80-91%. Chemical structures were elucidated on the basis of 1H and 13C NMR spectroscopic data and elemental analyses.