Formation of Trichloromethylated-1,3,5-triazines from Guanidine, Trichloroacetonitrile, and Isothiocyanates

Triazines have been defined as six-membered heterocyclic aromatic compounds of considerableinterest having three nitrogen atoms that are well known for a long time. The most importantmember of this group is 1,3,5-triazines that exist in the structure of many pesticidesand pigments and have widespread applications in the textile, plastic, and rubber industries.Most triazine derivatives are important medicinal compounds; some of them can act as antitumor[1]. Several synthetic methods for the preparation of these compounds have been reported[2], nevertheless, the preparation of polyfunctional and trichloromethylated 1,3,5-triazines is still a challenge. In this work, we describe a method based on the use of trichloroacetamidineresulting from trichloroacetonitrile and guanidine, as bidentate nucleophile andisothiocyanate as electrophile, to afford tricholoromethylated-1,3,5-triazine system [3]. Asshown in Scheme 1, the reaction of guanidine (1) and trichloroacetonitrile (2) in the presenceof isothiocyanates (3) at room temperature leads to production of 4.