Studies in spiroheterocycles: Part II~(dagger)-Synthesis and antibacterial activity of some novel spiro[indole-pyrazolines], spiro[indole-pyrimidines] and spiro[indole-1,5-benzodiazepines] containing 1,8-naphtyridine moiety

摘要

3-Acetyl-2-methyl-1,8-naphthyridine 1 on treatment with different isatins 2 gives the corresponding 3-hydroxy-3-(2-methyl-1,8-naphthyridine-3-carbonylmethyl)-indole-2-ones 4. Cyclocondensation of 4 with hydrazine hydrate, phenylhydrazine, urea, thiourea and o-phenylenediamine afford novel spiro[indole-pyrazolines] 5 and 6, spiro [indole-pyrimidinones] 7, spiro[indole-pyrimidinethiones] 8 and spiro[indole-1,5-benzodiazepines] 9 containing 1,8-naphthyridine moiety,respectively. THe structures of the compounds 3-9 have been established on the basis of their elemental analyses and spectral (IR,~1H NMR and mass) data. The compounds 4,6- and 8 have been tested for their antibacterial activity.