Synthesis of Unsymmetrical Trisubstituted 1,3,5-Triazines Compounds

A novel approach has been reported for the synthesis of 1,3,5-triazine with three distinct substituents. The synthesis of the pivotal intermediate 2-chloro-4-R1-6-R2-1,3,5-triazine plays a critical role in achieving 1,3,5-triazine with three different substituents. This article presents two innovative one-pot processes for synthesizing various substituted 2-chloro-4-R1-R2-1,3,5-triazines. In the first method, substituted benzoyl isocyanates were initially synthesized by reacting different amides with oxalyl chloride. Subsequently, 21 target products of 2-chloro-4-R1-R2-1,3,5-triazines compounds were obtained through the cyclization of substituted benzoyl isocyanates with benzamidine hydrochloride at relatively low temperatures and a one-pot chlorination reaction. The second method involved the synthesis of the same 21 compounds of 2-chloro-4-R1-R2-1,3,5-triazines by reacting benzamide with oxalyl chloride followed by cyclization with different amidine hydrochloride and then a one-pot chlorination reaction. Finally, a total of 35 different unsymmetrical trisubstituted 1,3,5-triazine compounds were successfully synthesized using various reactions.