Compounds Removed from the Condensation Reaction between 2-acetylpyridine and 2-formylpyridine. Synthesis, Crystal Structure and Biological Evaluation

• Main Authors: Roman Rusnac, Maria Botnaru, Nicanor Barba, Peter Petrenko, Yurii Chumakov, Aurelian Gulea
• Format: Article
• Language: English
• Published: Academy of Sciences of Moldova, Institute of Chemistry 2020-12-01
• Series: Chemistry Journal of Moldova: General, Industrial and Ecological Chemistry
• Subjects: 1,3-bis(pyridin-2-yl)prop-2-en-1-one; claisen-schmidt condensation; intramolecular aldol condensation; michael addition; substituted cyclohexanol
• Online Access: http://www.cjm.asm.md/sites/default/files/article_files/ChemJMold_10.19261cjm.2020.695-Rusnac.pdf
• ISSN: 1857-1727; 2345-1688

The research is devoted to the study of unexpected products that formed as a result of the condensation reaction between 2-acetylpyridine and 2-formylpyridine under the Claisen-Schmidt reaction conditions. As a result, a sequence of reactions leading to the following compounds has been proposed: 1,3-bis (pyridin-2-yl) prop-2-en-1-one (3); 1,3,5-tri (pyridin-2-yl) pentane-1,5-dione (4); (2,4-dihydroxy-2,4,6-tri(pyridin-2-yl)cyclohexyl)(pyridin-2-yl)methanone (5) and (4-hydroxy-2,4,6-tri(pyridin-2-yl)cyclohexane-1,3-diyl)bis(pyridin-2-ylmethanone) (6) as well as 2-formylpyridine (1) and 2-acetylpyridine (2). The plausible mechanism of these chemical transformations has been proposed. All the obtained compounds demonstrate moderate antimicrobial, antifungal and antioxidant activity.