Functionalized Pyrimidines from Alkynes and Nitriles: Application towards the Synthesis of Marine Natural Product Meridianin Analogs

Abstract

Fully substituted pyrimidine synthesis accomplished from alkynes and nitriles via BF3.Et2O mediated [2+2+2] cycloaddition. The substrate scope of the reaction was broad to include terminal alkynes to internal alkynes and aromatic nitriles to aliphatic nitriles furnished good to acceptable chemical yields. The marine alkaloid, meridianin analogs were synthesized successfully by utilizing this protocol. The pyrimidine analogues were also screened for their broad spectrum of antibacterial property against ten bacteria. Among the derivatives, 2,4 dimethyl-6-p-tolylpyrimidine (3b) has shown excellent inhibition potential against most of the tested organisms with a range of 9 to 21 mm zone of inhibition.