Multicomponent Electrocatalytic Selective Approach to Unsymmetrical Spiro[furo[3,2-<i>c</i>]pyran-2,5′-pyrimidine] Scaffold under a Column Chromatography-Free Protocol at Room Temperature

Abstract

Electrochemical synthesis suggested a mild, green and atom-efficient route to interesting and useful molecules, thus avoiding harsh chemical oxidizing and reducing agents used in traditional synthetic methods. Organic electrochemistry offers an excellent alternative to conventional methods of organic synthesis and creates a modern tool for carrying out organic synthesis, including cascade and multicomponent ones. In this research, a novel electrocatalytic multicomponent transformation was found: the electrochemical multicomponent assembly of arylaldehydes, N,N′-dimethylbarbituric acid and 4-hydroxy-6-methyl-2H-pyran-2-one in one pot reaction was carried out in alcohols in an undivided cell in the presence of alkali metal halides with the selective formation of substituted unsymmetrical 1′,3′,6-trimethyl-3-aryl-2′H,3H,4H-spiro[furo[3,2-c]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H)-tetraones in 73–82% yields. This new electrocatalytic process is a selective, facile and efficient way to obtain spiro[furo[3,2-c]pyran-2,5′-pyrimidines]. According to screening molecular docking data using a self-made Python script in Flare, all synthesized compounds may be prominent for different medical applications, such as breast cancer, neurodegenerative diseases and treatments connected with urinary tract, bones and the cardiovascular system.

Keywords

• electrolysis
• electrocatalysis
• multicomponent reaction
• mediators
• undivided cell
• electrosynthesis