8-Arylpurines and their ultraviolet absorption spectra

Dehydrocyclization of 4-amino-5-arylamidopyrimidines in polyphosphoric acid to 8-arylpurines was further investigated. Various other 8-arylpurines were synthesized by this new procedure in high purity and yield. The ultraviolet absorption spectra of the arylpurines and the corresponding acylamidopyrimidines were measured at pH 1, 7, and 13 at 0.1 molar ionic strength. The spectra of the purines resemble those of the corresponding acylamidopyrimidines and, to a lesser extent, the corresponding 4,5-diaminopyrimidines. The bathochromic shifts caused by different substituting groups in monosubstituted purines, in general, parallel the inductive effect of the substituting groups. The hyperchromicity and the inductive constant of the substituting groups assume a linear relationship, for substitution at either the 2 or 6 position. These changes in the wave length of maximum absorption and in the molar extinction coefficient caused by 2, 6 and 8 substitutions of the purines reported here are in agreement with previous studies by Mason.