Synthesis of a New Series of Pyridine and Fused Pyridine DerivativesReportar como inadecuado

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Chemistry Department, Faculty of Science, Princess Nora Bint Abdul Rahman University, Riyadh 11435, Saudi Arabia

Abstract The reaction of 4-methyl-2-phenyl-1,2-dihydro-6-oxo-5-pyridine- carbonitrile 1 with arylidene malononitrile afforded isoquinoline derivatives 2a,b. 6-Chloro-4-methyl-2-phenyl-5-pyridinecarbonitile 3 obtained by chlorination of compound 1 with phosphoryl chloride was converted into 6-amino-4-methyl-2-phenyl-5-pyridinecarbonitrile 4 and 6-hydrazido-4-methyl-2-phenyl-5-pyridinecarbonitrile 5 in good yield, through reactions with ammonium acetate and hydrazine hydrate, respectively. Treatment of 4 with ethyl acetoacetate, acetic anhydride, formic acid, urea and thiourea gave the corresponding pyrido 2,3-d pyrimidine derivatives 7–10a,b. A new series of 6-substituted-4-methyl-2-phenyl-5-pyridine carbonitriles 11–13 has been synthesized via reaction of 4 with phenyl isothiocyanate, benzenesulphonyl chloride and acetic anhydride. Treatment of 4 with malononitrile gave 1,8-naphthyridine derivative 14. The reactivity of hydrazide 5 towards acetic acid, phenylisothiocyanate and methylacrylate to give pyrazolo-3,4-b-pyridine derivatives 15–17 was studied. Treatment of 5 with acetic anhydride, phthalic anhydride and carbon disulphide gave pyridine derivatives 18,19 and 1,2,4-triazolo-3,4-a-pyridine derivative 20.

Keywords: pyridine derivatives; pyrido-2,3-d-pyrimidine; pyrazolo-3,4-b-pyridine pyridine derivatives; pyrido-2,3-d-pyrimidine; pyrazolo-3,4-b-pyridine

Autor: Siham AbdulRahman Al-Issa



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