Modern Organic Chemistry Research

Download PDF (303.8 KB) PP. 67 - 73 Pub. Date: April 20, 2017

DOI: 10.22606/mocr.2017.22005

• Karolina Wieszczycka, Krzysztof Bukowski^*
  Poznan University of Technology, Institute of Chemical Technology and Engineering, Berdychowo St. 4; 60-965 Poznan, Poland
• Grzegorz Framski
  
  Institute of Bioorganic Chemistry Polish Academy of Science, Noskowskiego St. 12,14; 61-704 Poznan, Poland

In this paper we report a three-stage synthesis of alkyl ethyl 2-oxo-2-(pyridin-2-, -3- and -4-yl)ethylphosphonates (2a-e, 3a-e, 4a-e) starting from commercially-available triethyl phosphite.Triethyl phosphite was first transesterified with alcohols in the presence of sodium catalyst to givethe alkyl diethyl phosphites (1b-e) in low to moderate yields. The Claisen condensation between 2-lithioalkylphosphonates and ethyl pyridine-2-,-3- and -4-carboxylate, followed by an Arbusov reactionwith methyl iodide, gave the final products in moderate yields. The structures of the products wereconfirmed by 1H-NMR, 13C-NMR, and 31P-NMR. Estimation of the pharmacotherapeutic potentialhas been accomplished for synthesized compounds on the basis of Prediction of Activity Spectra forSubstances (PASS).

Claisen condensation, synthesis, 2-oxo-2-pyridylethylphosphonates, bioactive compounds

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