Electrolysis of JV-heterocyclic compounds

The review on the electrolysis of JV-heterocyclic compounds by Lund in 1970 included a discussion on the polarographic behavior of quinazoline. The reduction of quinazoline was complicated by covalent hydration in acidic solution, because the hydrated species were not easily reduced. The anhydrous species in alkaline medium were reduced stepwise to dihydro and then to tetrahydroquinazoline, and the dihydro radical intermediate was capable of dimerization. The protonation rates of N-heterocycles in aqueous solution could be determined by polarographic techniques. The rates for quinazoline, and pyrimidine, however, were too fast for measurement which was consistent with predictions from quantum-chemical calculations. ... 

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