TY - JOUR
T1 - Synthesis and properties of 7-hydroxyxanthine and its derivatives
AU - Zvilichovsky, Gury
AU - Feingers, Judith
PY - 1976
Y1 - 1976
N2 - Use of an improved procedure for the synthesis of 7-hydroxyxanthine has enabled the synthesis of 7-hydroxy-1-methylxanthine and several 8-alkyl derivatives. The reactivity of 7-hydroxyxanthine and 7-hydroxy-1-methylxanthine towards acetic anhydride has been compared with that of 3-hydroxyxanthine. The 8-alkyl derivatives, which have the same electronic and tautomeric properties as the 8-unsubstituted compounds were more soluble in organic solvents. Reduction of the N-hydroxy-group in these derivatives gave xanthines soluble in organic solvents. U.v. and n.m.r. spectra and dissociation constants are discussed.
AB - Use of an improved procedure for the synthesis of 7-hydroxyxanthine has enabled the synthesis of 7-hydroxy-1-methylxanthine and several 8-alkyl derivatives. The reactivity of 7-hydroxyxanthine and 7-hydroxy-1-methylxanthine towards acetic anhydride has been compared with that of 3-hydroxyxanthine. The 8-alkyl derivatives, which have the same electronic and tautomeric properties as the 8-unsubstituted compounds were more soluble in organic solvents. Reduction of the N-hydroxy-group in these derivatives gave xanthines soluble in organic solvents. U.v. and n.m.r. spectra and dissociation constants are discussed.
UR - http://www.scopus.com/inward/record.url?scp=0016913951&partnerID=8YFLogxK
U2 - 10.1039/p19760001507
DO - 10.1039/p19760001507
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C2 - 987049
AN - SCOPUS:0016913951
SN - 1472-7781
SP - 1507
EP - 1511
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 14
ER -