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Abstract p-Diacetyl benzene 1 undergoes bromination to afford p-bromoacetyl phenacyl bromide 2. Compound 2 reacts with twofold excess of malononitrile to afford 2-{2- [4-(3,3 - Dicyanopropiony I )-pheny I] - 2-oxo-ethy l}- malononitrile3. Compound 3 could be cyclized to afford the l,4-phenylene-bis-furan derivative 4. Compound 3 reacts also with a twofold excess of hydrazine hydrate and phenyl hydrazine under dry conditions to afford the bis pyrazole derivatives 5a,b respectively. The reaction of Sa,b with the same reagents in refluxing dioxane/DMF( 4: 1) afforded the bis pyrazolopyridazine derivatives 7 a and 7b respectively. The azo coupling of compound 3 with arene diazonium salts afforded .the bis pyrazoly derivatives 9a-c. The ~-keto esters 10a;b react with benzaldehyde and malononitrile in a one pot synthesis to afford the pyran derivatives lla,b. These latter compounds react with hydrazine hydrate and urea derivatives to afford the pyrano[2,3-c ]pyrazoles 15a,b and the pyrano [2,3-d] pyrimidine derivatives 17a-d respectively. |