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Molecules 2012, 17(9), 10902-10915; doi:10.3390/molecules170910902

Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives

Chemistry Department, Faculty of Science, Princess Nora Bint Abdul Rahman University, Riyadh 11435, Saudi Arabia
Received: 8 June 2012 / Revised: 12 August 2012 / Accepted: 24 August 2012 / Published: 11 September 2012
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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 710a,b. A new series of 6-substituted-4-methyl-2-phenyl-5-pyridine carbonitriles 1113 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 1517 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
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Al-Issa, S.A. Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives. Molecules 2012, 17, 10902-10915.

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