Semicarbazone derivatives were obtained by Michael-type reaction between 1,3,5-tris(N,N-dialkylamino) benzenes, powerful carbon nucleopilic reagents, and 1-aminocarbonyl-1,2-diaza-1,3-butadienes. This reaction was carried out under very mild and neutral conditions at room temperature. Semicarbazones derivatives, under basic conditions, gave two different types of heterocycles: substituted pyrazolones or cinnoline derivatives. These two heterocylces are contemporaneously formed and the relative prevalence of one of the two cyclization reactions depends on the solvent used.
A novel synthesis of substituted pyrazolone and cinnoline derivatives via intramolecular cyclization reaction of semicarbazone compounds
TOZZI, SILVIA;BOGA, CARLA;DEL VECCHIO, ERMINIA;FORLANI, LUCIANO;ZANNA, NICOLA
2008
Abstract
Semicarbazone derivatives were obtained by Michael-type reaction between 1,3,5-tris(N,N-dialkylamino) benzenes, powerful carbon nucleopilic reagents, and 1-aminocarbonyl-1,2-diaza-1,3-butadienes. This reaction was carried out under very mild and neutral conditions at room temperature. Semicarbazones derivatives, under basic conditions, gave two different types of heterocycles: substituted pyrazolones or cinnoline derivatives. These two heterocylces are contemporaneously formed and the relative prevalence of one of the two cyclization reactions depends on the solvent used.File in questo prodotto:
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