Synthesis of 2-cyanoacrylates containing pyridinyl moiety under ultrasound irradiation

Abstract

Reaction of ethyl cyanoacetate with carbon disulfide and dimethyl sulfate in the presence of sodium methoxide in anhydrous methanol yields ethyl 2-cyano-3,3-dimethyl-thioacrylate, followed by the nucleophilic substitution with 2-amino-3-chloro-4-methylpyridine under ultrasonic irradiation affording the key intermediate, ethyl 3-(2-chloro-4-methylpyridin-3-ylamino)-2-cyano-3-methylthioacrylate. The title compounds were then obtained through the reaction of the key intermediate with the aliphatic amine under reflux condition. All the new structures were verified by elemental analysis, IR, 1 H NMR and mass spectra. In the MTT test, these new compounds were found to possess moderate antitumor activities against PC3 and A431 cells.

Synthesis, Antiviral and Antifungal Bioactivity of 2-Cyano-acrylate Derivatives Containing Phosphonyl Moieties

“…A large number of reports on the synthesis of cyanoacrylate derivatives exist due to their wide range of biological activities [3][4][5][6]. Some derivatives can serve not only as agrochemicals such as herbicides, insecticides, fungicides and plant virucides, but also as medicines such as antitumor agents.…”