Preparation of Polyfunctionally Substituted Pyridine-2(1<i>H</i>)-Thione Derivatives as Precursors to Bicycles and Polycycles  

作　　者：Fathi A. Abu-Shanab Sayed A. S. Mousa Sherif M. Sherif Mohamed I. Hassan 

机构地区：[1]Department of Chemistry, Faculty of Science, Al-Azhar University, Assiut, Egypt [2]Department of Chemistry, Faculty of Science, Gazan University, Gazan, KSA [3]Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt

出　　处：《International Journal of Organic Chemistry》2014年第5期319-330,共12页有机化学国际期刊（英文）

摘　　要：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.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.

关 键 词：Acetyl Acetone DMFDMA MALONONITRILE Dimmer BIPYRIDYL 5-Acetylpyridinethione 

分 类 号：O6[理学—化学]