2-Alkyl-4,6-dialkylamino-1,3,5-triazines via Grignard Alkylation of Cyanuric Chloride: An Aged Reaction Revisited

Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

“…In the literature, methods of synthesis of tris(aryl)-1,3,5-triazines by cyclotrimerization of aromatic nitriles in solvent-free conditions have been described [566,571]. In general, the best routes available to obtain trisubstituted 1,3,5-triazines are substitution reactions of chlorine atoms of cyanuric chloride with different nucleophiles [207,497,522,556,565,[573][574][575][576][577][578][579][580][581][582][583]; it is possible to substitute one, two or three selectively (Section 20.4.5.3).…”

“…Alkynyl-1,3,5-triazines 347 have been synthesized by reaction of cyanuric chloride 6 with Grignard reagents [583] or by Pd-catalyzed cross-coupling between alkynes and 345 [686,687].…”

Terminal alkyne-functionalized triazine by Sonogashira coupling: synthesis of a potential cell signalling inhibitor via click chemistry

“…1). Furthermore, Grignard alkynylation of 2,4,6-trichloro-1,3,5-triazine 3 (cyanuric chloride) was revisited, 10 allowing access to 2-(alk-1 0 -ynyl)-4,6-dialkylamino-1,3,5-triazines 4. Importantly, it appears that none of these papers mention the synthesis of triazines possessing the terminal acetylene group, required in our case for the Huisgen 1,3-dipolar cycloaddition reaction.…”

In Vitro Cytotoxic Activities of 2-Alkyl-4,6-diheteroalkyl-1,3,5-triazines: New Molecules in Anticancer Research

“…The preparation of 1,3,5-triazine derivatives 5 , 7 − 9 , 10 − 12 , , (Figure ) and 17 − 20 18 (Figure ) has been described elsewhere; 6 , 13 , 14 , 16 (Figure ) were synthesized according to reported procedures, − while derivatives 21 − 23 (Figure ) were prepared in the context of this investigation by using, for the first time, a Pd-mediated Stille cross-coupling reaction between 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and suitable organotin compounds; the experimental details of the preparation and characterization of new products are available as Supporting Information. Compound 15 is commercially (Sigma-Aldrich) available.…”