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Modern Organic Chemistry Research
MOCR > Volume 2, Number 2, May 2017

Synthesis and Spectral Analysis of Pyridine Derivates

Download PDF  (310.1 KB)PP. 41-47,  Pub. Date:May 15, 2017
DOI: 10.22606/mocr.2017.22002

Author(s)
Aleksandra Wojciechowska, Karolina Wieszczycka, Grzegorz Framski
Affiliation(s)
Poznan University of Technology, Institute of Chemical Technology and Engineering, Berdychowo St. 4, 60-965 Poznan, Poland

Poznan University of Technology, Institute of Chemical Technology and Engineering, Berdychowo St. 4, 60-965 Poznan, Poland

Institute of Bioorganic Chemistry Polish Academy of Science, Noskowskiego St. 12,14, 61-704 Poznan, Poland
Abstract
The present study described a detailed investigation of the synthesis of novel quaternary pyridinium salts: derivates of 1-(3-pyridine)undecane-1-one (1-propyl-3-undecanoylpyridinium bromide and 1-propyl-3-undecanoylpyridinium chloride) and N-decyloxypyridine-3-carboximidamide (3-[1-(N-decyloxyimine)ethyl]-1-propylpyridinium chloride and 3-[1-(N-decyloxyimine)ethyl]-1-propylpyridinium bromide). The structures of the products were confirmed by spectral(1H-NMR, 13C-NMR, FT-IR) analysis, mass spectrometry methods. Estimation of the pharmacotherapeutic potential has been accomplished for synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASS programe).
Keywords
Quaternary pyridinium salts, synthesis, quarterisation reaction, O-alkylation, prediction of activity
References
  • [1]  N. Menschutkin, “Beitr?gen zur kenntnis der affinit?tskoeffizienten der alkylhaloide und der organischen amine”, Zeitschrift für Physikalische Chemie, vol. 5, pp. 589–601, 1890.
  • [2]  C. R. Noller, R. Dinsmore, “The reaction of alkyl bromides with pyridine“, Journal of the American Chemical Society, vol. 54, pp. 1025–1034, 1932.
  • [3]  H. T. Clarke, “The relation between reactivity and chemical constitution of certain halogen compounds”, Journal of the Chemical Society, vol. 97. pp. 416–429, 1910.
  • [4]  C. A. Winkler, C. N. Hinschelwood, “The factors determining the velocity of reactions in solution. The formation of quaternary ammonium salts in benzene solution”, Journal of the Chemical Society, pp. 1147–1151, 1935.
  • [5]  D. L. Comins, S. O’Connor, R. S. Al-awar, “Pyridines and their Benzo Derivatives: Reactivity at the Ring”, Comprehensive Heterocyclic Chemistry III, Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, vol.7, pp.41-99, 2008.
  • [6]  R. Miklá?, N. Miklá?ová, M. Bukovsky, B. Horváth, J. Kubincová , F. Devínsky, ”Synthesis, surface and antimicrobial properties of some quaternary ammonium homochiral camphor sulfonamides”, European Journal of Pharmaceutical Sciences, vol. 65, pp. 29–37, 2014.
  • [7]  P. Madaan P, V. K. Tyagi, ”Quaternary pyridinium salts: a review”, Journal of Oleo Science, vol. 57, no. 4, pp. 197-215, 2008.
  • [8]  Y. H. Kim, G. Sun, “Functional finishing of acrylic and cationic dyeable fabrics: intermolecular interactions”, Textile Research Journal, vol. 72, pp. 1052–1056, 2002.
  • [9]  S. Shirakawa, K. Liu, K. Maruoka, “Catalytic asymmetric synthesis of axially chiral o-odoanilides by phasetransfer catalyzed alkylations”, Journal of the American Chemical Society, vol. 134, no. 2, pp. 916–919, 2002.
  • [10]  M. Jadhav, R. S. Kalhapure, S. Rambharose, C. Mocktar, T. Govender, “Synthesis, characterization and antibacterial activity of novel heterocyclic quaternary ammonium surfactants”, Journal of Industrial and Engineering Chemistry, article in press, 2016.
  • [11]  M. V. Pugachev, N. V. Shtyrlin, S. V. Sapozhnikov, L. P. Sysoeva, A. G. Iksanova, E. V. Nikitina, R. Z. Musin, O. A. Lodochnikova, E. A. Berdnikova, Y. G. Shtyrlin, “Bis-phosphonium salts of pyridoxine: The relationship between structure and antibacterial activity”, Bioorganic & Medicinal Chemistry, vol. 21, pp. 7330–7342, 2013.
  • [12]  B. Sarkar, Y. Xi, M. Megharaj, R. Naidu, “Orange II adsorption on palygorskites modified with alkyl trimethylammonium and dialkyl dimethylammonium bromide—an isothermal and kinetic study”, Applied Clay Science, vol. 51, pp. 370–374, 2011.
  • [13]  B. Dmochowska, J. Piosik, A. Woziwodzka, K.Sikora, A. Wi?niewski, G. W?grzyn, “Mutagenicity of quaternary ammonium salts containing carbohydrate moieties”, Journal of Hazardous Materials, vol. 193, pp. 272–278, 2011.
  • [14]  J. Krysiński, J. Placzek, A. Skrzypczak, B. Predki, ?Analysis of relationships between structure, surface properties, and antimicrobial activity of quaternary ammonium chlorides”, QSAR & Combinatorial Science, vol. 28, pp. 995–1002, 2009.
  • [15]  E. Grabińska-Sota, “Genotoxicity and biodegradation of quaternary ammonium salts in aquatic environments”, Journal of Hazardous Materials, vol. 195, pp. 182–187, 2011.
  • [16]  E. Ob??k , A. Piecuch, A. Krasowska, J. ?uczyński, ?Antifungal activity of gemini quaternary ammonium salts” Microbiological Research, vol.168, pp. 630–638, 2013.
  • [17]  E. Abele, R. Abele, E. Lukevics, “Pyridine oxime: synthesis, reactions and biological activity. Review”, Chemistry of Heterocyclic Compounds, vol. 39, no. 7, pp. 825–865, 2003.
  • [18]  P. Madaan, V. K. Tyagi, “Quaternary Pyridinium Salts: A Review”, Journal of Oleo Science, vol. 57, pp. 197-215, 2008.
  • [19]  W. Sliwa, “Quaternary salts of pyridines and related compounds”, Current Organic Chemistry, vol. 7, pp. 995-1048, 2003.
  • [20]  K. Wieszczycka, A. Wojciechowska, M. Krupa, R. Kordala-Markiewicz, “Quaternary pyridinium ketoximes zinc extractants from chloride solutions”, Journal Chemical Engineering Data, vol. 11, pp. 3207-3215, 2013.
  • [21]  K. Wejman-Gibas, K. Wieszczycka, A. Wojciechowska, K. Ochromowicz, P. Pohl, “Extraction of molybdenum(VI) from sulfate media by 3-pyridineketoxime and its quaternary salts”, Separation and Purification Technology, vol. 158, pp. 71-79, 2016.
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