Collect. Czech. Chem. Commun.
1994, 59, 1153-1174
https://doi.org/10.1135/cccc19941153
Synthesis of N-(3-Azido-2-hydroxypropyl), N-(3-Phthalimido-2-hydroxypropyl) and N-(3-Amino-2-hydroxypropyl) Derivatives of Heterocyclic Bases
Maria Spassova, Hana Dvořáková, Antonín Holý, Miloš Buděšínský and Milena Masojídková
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
Abstract
Alkylation of heterocyclic bases with azidomethyloxirane (I) under basic catalysis with potassium or cesium carbonate afforded N-(3-azido-2-hydroxypropyl) derivatives II. Hydrogenation of these compounds over palladium on carbon gave the corresponding 3-amino-2-hydroxypropyl derivatives III. The same compounds III were prepared by alkylation of heterocyclic bases with phthalimidomethyloxirane (VII) in the presence of cesium carbonate and subsequent reaction of the formed N-(3-phthalimido-2-hydroxypropyl) derivatives VIII with hydrazine. The phthalimido derivatives VIII are easily hydrolyzed already in weakly alkaline aqueous medium to give 9-[3-(o-carboxybenzoylamino)-2-hydroxypropyl] derivatives IX and X.
