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Preparation of Polyfunctionally Substituted Pyridine-2(1<i>H</i>)-Thione Derivatives as Precursors to Bicycles and Polycycles
Department of Chemistry, Faculty of Science, Gazan University, Gazan, KSA
Department of Chemistry, Faculty of Science, Al-Azhar University, Assiut, Egypt
Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt
Department of Chemistry, Faculty of Science, Al-Azhar University, Assiut, Egypt
- 1 Department of Chemistry, Faculty of Science, Gazan University, Gazan, KSA
- 2 Department of Chemistry, Faculty of Science, Al-Azhar University, Assiut, Egypt
- 3 Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt
- 4 Department of Chemistry, Faculty of Science, Al-Azhar University, Assiut, Egypt
International Journal of Organic Chemistry·Volume 04 (2014)·Pages 319–330·Published 26 December 2014·DOI10.4236/ijoc.2014.45035
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Abstract
Reaction of acetylacetone with 1 mole of dimethylformamide dimethyl acetal (DMFDMA) affords enamine 2a which reacts with cyanothioacetamide to give pyridinethione 3a. Pyridinethione 3a reacts with methyl iodide, halogenated compounds, aromatic aldehyde and malononitrile/elemental sulfur to yiled compounds 7-10 respectively. Reactions of thioether 7 in ethanolic K2CO3, 1 mole DMFDMA and 4-(dimethylamino)benzaldehyde give compounds 11, 13, 14 respectively. Enaminone 12 can be prepared by reaction of compound 11 with DMFDMA. We have demonstrated some reactions in order to show the potential usefulness of the prepared compounds for the preparation of new bipyridyl compounds 15, 16, 18, bicyclic compounds 17 and uncommon tricyclic compounds 20, 21, 22 and 23 respectively using DMFDMA.
KeywordsAcetyl AcetoneDMFDMAMalononitrile DimmerBipyridyl5-Acetylpyridinethione
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