The synthesis of some new derivatives of 1, 7-dimethylxanthine

Abstract

We have synthesized a group of new 8-substituted 1, 7-dimethylxanthines which are of interest for biological investigation as very close structural analogs of some 8-substituted theobromine derivatives obtained previously. In particular, we have carried out the conversion of 8-hydroxymethyl-1, 7-dimethlxanthine (I) [1] into 8-chloromethyl-1, 7-dimethylxanthine (II) and from this, by heating it for 6 hours with an excess of diethylamine or by condensing it with sodioacetylaminomalonic ester in ethanol we have obtained 8-diethylaminomethyl-1, 7-dimethylxanthine (III) and its hydrochloride (compare [2]) or 8-(β-acetylamino-β, β-diethoxycarbonylethyl)-1, 7-dimethylxanthine (IV). The hydrolytic cleavage of the latter, accompanied by partial decarboxylation, led to 1, 7-dimethyl-8-xanthinylalanine (V) (cf. [3]).