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Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives

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-meth...

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Autor principal: Al-Issa, Siham AbdulRahman
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268994/
https://www.ncbi.nlm.nih.gov/pubmed/22968474
http://dx.doi.org/10.3390/molecules170910902
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author Al-Issa, Siham AbdulRahman
author_facet Al-Issa, Siham AbdulRahman
author_sort Al-Issa, Siham AbdulRahman
collection PubMed
description 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.
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spelling pubmed-62689942018-12-12 Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives Al-Issa, Siham AbdulRahman Molecules Article 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. MDPI 2012-09-11 /pmc/articles/PMC6268994/ /pubmed/22968474 http://dx.doi.org/10.3390/molecules170910902 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Al-Issa, Siham AbdulRahman
Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives
title Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives
title_full Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives
title_fullStr Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives
title_full_unstemmed Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives
title_short Synthesis of a New Series of Pyridine and Fused Pyridine Derivatives
title_sort synthesis of a new series of pyridine and fused pyridine derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268994/
https://www.ncbi.nlm.nih.gov/pubmed/22968474
http://dx.doi.org/10.3390/molecules170910902
work_keys_str_mv AT alissasihamabdulrahman synthesisofanewseriesofpyridineandfusedpyridinederivatives