Artículos de revistas
Reaction of diphenylcyclopropenone with N-acylamidine derivatives. Synthetic and mechanistic implications
Registro en:
Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 12, n. 4, p. 481-484, 2001.
0103-5053
S0103-50532001000400006
10.1590/S0103-50532001000400006
Autor
Cunha, Silvio
Kascheres, Albert
Institución
Resumen
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. A reatividade de ciclopropenonas frente a derivados de N-acilamidinas foi investigada. Difenilciclopropenona reagiu com N-benzoilacetamidina e com N-(metoxicarbonil)benzamidina formando 1,2-diidro-3H-pirrol-3-onas em rendimentos moderados, porém alquilfenilciclopropenonas não reagiram com os mesmos nucleófilos investigados. A teoria dos orbitais moleculares de fronteira foi empregada para racionalizar a formação dos produtos. 481 484 Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)