Reaction of diphenylcyclopropenone with N-acylamidine derivatives. Synthetic and mechanistic implications

In this work, the reactivity of cyclopropenones toward N-acylamidine derivatives was investigated. Diphenylcyclopropenone reacted with N-benzoylacetamidine and N-(methoxycarbonyl)benzamidine affording 1,2-dihydro-3H-pyrrol-3-ones in moderate yields. However, alkylphenylcyclopropenone did not react. The formation of the compounds is examined mechanistically within frontier molecular orbital considerations.