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Synthesis and properties of 7‐hydroxy‐8‐phenylxanthine and its derivatives. Disproportionation to derivatives of 8‐phenylxanthine and 6‐amino‐5‐nitrosouracil
Author(s) -
Zvilichovsky Gury,
Garbi Herzel,
Nemes Eliahu
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190139
Subject(s) - disproportionation , chemistry , benzaldehyde , ring (chemistry) , medicinal chemistry , organic chemistry , catalysis
8‐Phenyl, 8‐( p ‐methoxyphenyl) and 8‐( p ‐chlorophenyl)‐7‐hydroxyxanthine were synthesized by ring closure of 6‐amino‐5‐nitrosouracil with benzaldehyde, p ‐methoxybenzaldehyde and p ‐chlorobenzaldehyde, respectively. The disproportionation of these products to the corresponding 8‐phenylxanthines and 6‐amino‐5‐nitrosouracil was studied. The dependence of the rate of the reaction on the various substituents was studied. The disproportionation reaction is inhibited by the polarophilic ethyl acetylenedicarboxylate and enhanced by phosphate.