Abstract
The deuterium exchange rate of the α-methylene of deoxyvasicinone (1) and mackinazolinone (2) and their seven- (3) and eight-membered (4) homologs was studied in neutral, acidic, and basic media. It was found that the exchange rate depended on the number of methylenes in the polymethylene ring and the medium. The deuterium exchange rate decreased in the order 2→1→3→4 and was slowest in media close to neutral. The results agreed with those for the reactions of 1–4 with bromine in acidic medium, condensation with substituted aromatic and heterocyclic aldehydes, and acylation by aromatic acid chlorides. Several trends in the reactivity of the tricyclic quinazolin-4-ones were discovered.
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