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

Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives

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Received: 8 June 2012; in revised form: 12 August 2012 / Accepted: 24 August 2012 / Published: 11 September 2012
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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 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
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MDPI and ACS Style

Al-Issa, S.A. Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives. Molecules 2012, 17, 10902-10915.

AMA Style

Al-Issa SA. Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives. Molecules. 2012; 17(9):10902-10915.

Chicago/Turabian Style

Al-Issa, Siham AbdulRahman. 2012. "Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives." Molecules 17, no. 9: 10902-10915.

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