Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones

Abstract

A number of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones from cyanoacetamide and the corresponding alkyl ethyl acetoacetates were synthesized according to modified literature procedures. The alkyl ethyl acetoacetates were obtained by the reaction of C-alkylation of ethyl acetoacetate. An investigation of the reaction conditions for the synthesis of 4-methyl-3-cyano-6-hydroxy-2-pyridone from cyanoacetamide and ethyl acetoacetate in eight different solvents was also performed. The ultraviolet absorption spectra of synthesized pyridones were measured in nine different solvents in the range 200–400 nm. The effects of solvent polarity and hydrogen bonding on the absorption spectra are interpreted by means of linear solvation energy relationships using a general equation of the form n = n0 + sp* + aa + bb, where p* is a measure of the solvent polarity, a is the scale of the solvent hydrogen bond donor acidities and b is the scale of the solvent hydrogen bond acceptor basicities.

Keywords

• alkylation
• ethyl acetoacetate
• alkyl ethyl acetoacetates synthesis
• 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones
• spectroscopy
• cyclization
• ultraviolet absorption spectra
• solvent effects
• linear solvation energy relationships