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

Autor:	Fathi A. Abu-Shanab, Sherif M. Sherif, Mohamed Ibrahim Abu Hassan, Sayed A. S. Mousa
Rok vydání:	2014
Předmět:	chemistry.chemical_classification Benzaldehyde chemistry.chemical_compound chemistry Thioether Bicyclic molecule Acetylacetone Pyridine Aldehyde Medicinal chemistry Enamine Malononitrile
Zdroj:	International Journal of Organic Chemistry. :319-330
ISSN:	2161-4695 2161-4687
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::fb6c3819689b6e128d632acf70fa0056 https://doi.org/10.4236/ijoc.2014.45035 Zobrazit plný text záznamu