Synthesis of N-(3-Azido-2-hydroxypropyl), N-(3-Phthalimido-2-hydroxypropyl) and N-(3-Amino-2-hydroxypropyl) Derivatives of Heterocyclic Bases
- 1 January 1994
- journal article
- Published by Institute of Organic Chemistry & Biochemistry in Collection of Czechoslovak Chemical Communications
- Vol. 59 (5) , 1153-1174
- https://doi.org/10.1135/cccc19941153
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.Keywords
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