Synthesis of new 3-acryloyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline derivatives and their behaviour towards some nucleophiles

Abstract

Many new 3-acryloyl-1,2-dihydro-4-hydroxy-1-methyl-2-quinolone derivatives have been synthesized. The addition of a series of aromatic amines and thiols to the activated carbon - carbon double bond of the acryloyl side chain is described. The behaviour of some of these acryloyl derivatives towards 1,2-bifunctional nucleophiles: hydrazine, phenylhydrazine, and hydroxylamine, has been investigated and cyclocondensation reactions were found to take place, affording 3-(3-pyrazolinyl/isoxazolinyl)-2-quinolones. Addition of bromine to the 3-(5-styryl-3-pyrazolinyl/isoxazolinyl)-2-quinolones furnished the corresponding 1,2-dibromophenethyl derivatives which upon cyclization with o-phenylenediamine and/or o-aminothiophenol afforded novel heterotricyclic isolated systems of expected biological activity.