Reactivity of 3-cinnamoyl1-phenyl-2,4 [1H,3H] - quinoline-dione towards oxidation and oximation reactions Formation of fused heterocyclic quinolines

ABSTRACT

Acetyl-1,2,3,4-tetrahydro-2,4-dioxo-l-phenylquinoline [I] was condensed with benzaldehyde, crotonaldehyde and chloral hydrate to give he corresponding l-phenyl-3-substituted-2,4-[lH,3H]- quinolinediones [IIa-c]. Treatment of compound Ha with aniline gave 1-phenyl-3-[N-phenylcinnamoyl]-2,4 [lH,3H]-quinolinedione [IId]. In an alternative procedure compounds Ild-f were obtained via the condensation of anil, l-phenyl-3-[N- phenylcinnamoyl] 2,4-[lH,3H]-quinolinedione [IH]W, with the appropriate aldehyde namely, benzaldehyde, anisaldehyde and m-chlorobenzaldehyde to give l-phenyl-3-[N-substituted cinnamidoyl]-2,4 [lH,3H]-quinolinedione [Ild-f], respectively. The structure of compounds Ild-f was confirmed through their IR spectral data which showed bands at 3600-3300 [O H and N H] and at 1320 cm[-1][tert.-amine], besides their correct elemental analysis: