Y. Iwanami, T. Seki
Sep 1, 1972
Citations
0
Influential Citations
10
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Phenacyl derivatives of two naturally-occurring pteridines and their 4-amino analogues (III and V) have been synthesized for their structural study. Since these compounds are obtained by the condensation of ethyl benzoylpyruvates (II) with tri- or tetraaminopyrimidine (I), a carbon-nitrogen double bond, which is adjacent to the phenyl group of the side chain, may be expected in the ring (Remark: Graphics omitted.). However, their NMR spectra show that the double bonds of all the products are displaced onto the side chain (Remark: Graphics omitted.), the carbonyl of which is hydrogen-bonded with the secondary amino group thereby formed. This form of V makes striking contrast to alkyl isoxanthopterin-6-acetates (X), in which the corresponding double bond remains undisplaced. The intermediate products of V (IV) and V were hydrolyzed with acid or alkali into 6-methyl-isoxanthopterin (VI) and benzoic acids (VII).