Synthesis and Reactions of Halo-,Arylazo-substituted 3-(3-(1-naphthyl)acryloyl)tropolones.Formation of(Naphthalen-1-yl)vinyl)substituted Heterocycle-fused Troponoid Compounds

摘要

The starting substrate 3-(3-(1-naphthyl)acryloyl)tropolone(3)was achieved by the aldol condensation reaction of 3-acetyltropolone with 1-naphthaldehyde.Compound 3 reacted with bromine to afford 7-bromo-3-(3-(1-naphthyl)acryioyl)tropolone(4),5,7-dibromo-3-(3-(1-naphthyl)acryloyl)tropolone(5)according to the molar ratio of the reactants.Iodination of 3 gave 7-iodo-3-(3-(1-naphthyl)acryloyl)tropolone(6).Azo-coupling reactions of 3 gave the 5-arylazo-3-(3-(1-naphthyl)acryloyl)tropolones(7-8).Compounds 3,4,6 reacted respectively with hydroxyamine to give the corresponding 3-[2-(1-naphthyl)vinyl]-8H-cyclohepta[d]isoxazol-8-ones(9-11).The reactions of 3,5 with phenylhydrazine and substituted phenylhydrazines gave 3-[2-(1-naphthyl)vinyl]-1-phenylcyclohepta[c]pyrazol-8(1H)-ones(12-18).