化学療法剤の研究 第19報

p-Hydroxy-benzenesulfonamide誘導体の分子内轉位について その5

抄録

(1) It was found that when p-{pyrimidyl-(6)}-oxy-benzenesulfonamide, obtained by the condensation of p-hydroxybenzenesulfonamide and 6-chloropyrimidine, is heated and fused in the presence of alkali carbonate, pyrimidyl-(6) radical undergoes rearrangement to N to form 6-(p-hydroxybenzenesulfamino)-pyrimidine.
(2) when p-{pyrimidyl-(2 or 6)}-oxy-benzenesulfonamides are heated and fused with 2- or 6-chloropyrimidines in the presence of alkali carbonate, O, N-dipyrimidyl compounds are formed. In this condensation, two kinds of reactions were found to take place. In one reaction, the pyrimidyl radical in the para position does not undergo rearrangement to N but chloropyrimidine condenses with sulfonamide radical to form a dipyrimidyl compound. In the other, the initial pyrimidyl radical attached to the ortho position undergoes intramolecular rearrangement to N and a secondary pyrimidyl radical reacts with the newly formed OH radical to yeild a dipyrimidyl compound.