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Synthesis of New 3-Acryloyl-l,2-dihydro-4-hydroxy-l-rnethyl-2-oxoquinoline Derivatives and their Behaviour towards Some Nucleophiles

S. S. Ibrahim, H. A. Allimony, and E. S. Othman

Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, Egypt


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.

Full paper in Portable Document Format: 511a33.pdf


Chemical Papers 51 (1) 33–42 (1997)

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