Chemistry Journal of Moldova

COMPOUNDS REMOVED FROM THE CONDENSATION REACTION BETWEEN 2-ACETYLPYRIDINE AND 2-FORMYLPYRIDINE. SYNTHESIS, CRYSTAL STRUCTURE AND BIOLOGICAL EVALUATION

Author(s):

Roman Rusnac, Maria Botnaru, Nicanor Barba, Peter Petrenko, Yurii Chumakov, Aurelian Gulea


Field: Organic chemistry
Type: Research paper
Pages: 11
Keywords:

1,3-bis(pyridin-2-yl)prop-2-en-1-one, Claisen-Schmidt condensation, intramolecular aldol condensation, Michael addition, substituted cyclohexanol.


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DOI: http://dx.doi.org/10.19261/cjm.2020.695   
 
Graphical Abstract: 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 mechanism of these chemical transformations has been proposed. All the obtained compounds demonstrate moderate antimicrobial, antifungal and antioxidant activity.


 

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