Pteridines, XCVI. Synthesis and Reactions of 6-(1,2,3-Trihydroxypropyl)pteridines

Abstract

Summary Various hydropyrano [3.2-g] pteridines (7, 10, 12, 21 , 33) were oxidized to the corresponding 6-(1,2,3- trihydroxypropyl)pteridine derivatives (8,9, 11, 13,32, 34), which are valuable intermediates for the synthesis of new 6-substituted pteridines (15 - 46). Periodate oxidation led to pteridine-6-carboxaldehydes (15, 16, 17, 38), which easily formed oximes (19 - 22, 39, 40). The aldehydes were further oxidized to 6-carboxylic acids (25,26,42) or reduced to 6-hydroxymethyl derivatives (27, 28, 43). Reductive condensations of the aldehydes (15, 16, 38) with p-aminobenzoylglutamic acid afforded folic acid analogues (29, 30, 44). Dehydration of the oximes (19, 20, 39) resulted in the formation of 6-carbonitriles (23, 24, 41, 46). The newly synthesized compounds were characterized by elemental analysis and by UV and NMR spectra.