Solvent Free Synthesis and 1,3-Dipolar Cycloaddition Reactions of N-Methyl-4- (Trimethylsilyl)-C-Phenyl Nitrone and Potential Anticancer Activities of Cycloadducts

Synthesis and cycloaddition reactions of N-Methyl-4-(Trimethylsilyl)-C-phenyl nitrone using mechanochemical procedure has been reported. Trimethyl substituent is chosen as this group is known to enhance nitrone geration and anticarcinogenic activities in cycloadducts. Trimethylsilyl group at 4-position of the phenyl ring activates aldehyde group and thereby the development of N-Methyl-4-(trimethylsilyl)-C-phenyl nitrone is much faster than other nitrones A notable change in reaction rate as well as yields of the trimethylsilylnitrone and trimethylsilyl cycloadducts has been observed comparing to microwave and coventional cycloaddition procedures. Solid phase mechanochemical procedure thus found to be more suitable than other greener techniques. The present study reports synthesis of N-Methyl-4-(Trimethylsilyl)-C-phenyl nitrone and their cycloaddition reactions with activated alkenes and electron deficient alkynes. Few synthesized new trimethylsilyl cycloadducts found to exhibit significant anticancer activities too.