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Multicomponent reaction of conjugated enynones with malononitrile and sodium alkoxides: Complex reaction mechanism of the formation of pyridine derivatives
Authors:Anastasiya V Kuznetcova  Ivan S Odin  Alexander A Golovanov  Iakov M Grigorev  Aleksander V Vasilyev
Institution:1. Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russia;2. Research Laboratory No. 13 of Organic Synthesis and Analysis of them. S.P. Korshunov, Togliatti State University, Belorusskaya ul., 14, Togliatti, 445667, Russia;3. Department of Chemistry, Chemical Processes and Technologies, Togliatti State University, Belorusskaya ul., 14, Togliatti, 445667, Russia;4. Educational Research Center of Chemistry of Research Park of Saint Petersburg State University, Universitetskiy pr., 26, Saint Petersburg, Petrodvoretz, 198504, Russia;5. Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per., 5, Saint Petersburg, 194021, Russia
Abstract:Reaction of conjugated enynones,1,5-diarylpent-2-en-4-yn-1-ones, with malononitrile and sodium alkoxides in the corresponding alcohols at room temperature for 3–23 h results in the formation of two types of compounds (E)-/(Z)-6-aryl-4-(2-arylethenyl)-2-alkoxypyridine-3-carbonitriles (substituted nicotinonitriles), as the major reaction products in yields up to ca. 40–80%, and 6-aryl-4-arylethynyl-2-alkoxypyridines, as the minor reaction products in yields of 5–17%. Plausible mechanism of this complex and multistep reaction is discussed. The obtained pyridines possess fluorescent properties.
Keywords:Corresponding author  Department of Organic Chemistry  Institute of Chemistry  Saint Petersburg State University  Universitetskaya nab    7/9  Saint Petersburg  199034  Russia    Conjugated enynones  Pyridines  Nicotinonitriles  Reaction mechanism  Fluorescence
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