SYNTHESIS OF NEW LOYL-1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXOQUINOLINE DERIVATIVES AND THEIR BEHAVIOR TOWARDS SOME NUCLEOPHILES

Many new cryloyl-1,2-dihydro-4-hydroxy-1-methyl-2-quinolone derivative s have been synthesized. The addition of a series of aromatic amines a nd thiols to the activated carbon-carbon double bond of the acryloyl s ide chain is described. The behaviour of some of these acryloyl deriva tives towards 1,2-bifunctional nucleophiles: hydrazine, phenylhydrazin e, and hydroxylamine, has been investigated and cyclocondensation reac tions were found to take place, affording 3-(3-pyrazolinyl/isoxazoliny l)-2-quinolones Addition of bromine to the (5-styryl-3-pyrazolinyl/iso xazolinyl)-2-quinolones furnished the corresponding 1,2-dibromopheneth yl derivatives which upon cyclization with o-phenylenediamine and/or o -aminothiophenol afforded novel heterotricyclic isolated systems of ex pected biological activity.