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

  1. Roman Vasile RusnacORCID Logo,
  2. Maria Stefan Botnaru,
  3. Nicanor Barba,
  4. Peter Alexei Petrenko,
  5. Yurii Chumakov and
  6. Aurelian Petru Gulea

Submitting author affiliation: Moldova State University, Chisinau, Moldova

Beilstein Arch. 2019, 2019145. doi:10.3762/bxiv.2019.145.v1

Published 18 Nov 2019

  • Preprint

Abstract

Two new carbonyl compounds (5-6) were synthesized and spectrally characterized. The reaction mechanism for obtaining the new carbonyl compounds (5-6) was proposed following the analisis retrosintetis reactions of the products and confirmed by 1H and 13C-NMR. Synthesized carbonyl compounds (3-6) can serve as precursors (carbonyls) in the synthesis of thiosemicarbazones, which exhibit a wide range of biological properties. Due the condensation reaction between 2-acetylpyridine and 2-formylpyridine, catalysed with Na2CO3 in aqueous solution and microwave irradiation at 480 W, the product 1,3-bis(pyridin-2-yl)prop-2-en-1-one (3) in a good yield is obtained. By separation on the silica gel column, three products (4-6) were removed. Characterization of novel condensation products between 2-acetylpyridine and 2-formylpyridine was performed by FTIR-ATR spectroscopy, 1H and 13C-NMR spectroscopy, and further confirmed by single crystal X-ray diffraction. Compound (5) crystallise in the space group P-1 and compound (6) in the space group P21/c. Based on the spectral data and X-ray crystallography analysis of the eliminated products, the succession of reactions resulting in compounds (3-6) from (1) and (2) were proposed. Finally, synthetic methods for the preparation of substituted cyclohexanol derivatives have also been proposed. The obtained compounds exhibit moderate antimicrobial and antifungal activity. Antioxidant activity of compounds (4-6) was also studied.

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

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When a peer-reviewed version of this preprint is available in the Beilstein Journals, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Rusnac, R. V.; Botnaru, M. S.; Barba, N.; Petrenko, P. A.; Chumakov, Y.; Gulea, A. P. Beilstein Arch. 2019, 2019145. doi:10.3762/bxiv.2019.145.v1

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