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.
XXIII Corso Estivo "A. Corbella" Seminari di Sintesi Organica
O18
O18
S. Tozzi; O. A. Attanasi; C. Boga; L. De Crescentini; E. Del Vecchio; G. Favi; L. Forlani; F. Mantellini; N. Zanna
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/62147
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