SYNTHESIS OF N-(3-AZIDO-2-HYDROXYPROPYL), N-(3-PHTHALIMIDO-2-HYDROXYPROPYL) AND N-(3-AMINO-2-HYDROXYPROPYL) DERIVATIVES OF HETEROCYCLIC BASES

Alkylation of heterocyclic bases with azidomethyloxirane (I) under bas ic catalysis with potassium or cesium carbonate afforded N-(3-azido-2- hydroxypropyl) derivatives II. Hydrogenation of these compounds over p alladium on carbon gave the corresponding 3-amino-2-hydroxypropyl deri vatives III. The same compounds III were prepared by alkylation of het erocyclic bases with phthalimidomethyloxirane (VII) in the presence of cesium carbonate and subsequent reaction of the formed N-(3-phthalimi do-2-hydroxypropyl) derivatives VIII with hydrazine. The phthalimido d erivatives VIII are easily hydrolyzed already in weakly alkaline aqueo us medium to give 9-[3-(o-carboxybenzoylamino)-2-hydroxypropyl] deriva tives IX and X.