One-pot synthesis of triazines as potential agents affecting cell differentiation

Abstract

This paper outlines the synthesis of a number of structural analogs of 3-[(4,6-diphenoxy-1,3,5-triazin-2-yl)amino]benzoic acid which represent compounds with potential cardiogenetic activity. A one-pot protocol was developed for swift functionalization of the 1,3,5-triazine core without the need of isolating intermediates. The developed route starts from readily available 2,4,6-trichloro-1,3,5-triazine, displacing the chlorine atoms sequentially by aryloxy, arylamino, or arylthio moieties to enable access to molecules with three different substituents of this type in good yields. To facilitate purification, tert-butyl, methyl, and ethyl ester derivatives of the target compounds were initially synthesized. The tert-butyl esters could be readily hydrolyzed to the desired compounds, while reduction of the methyl and ethyl esters gave the corresponding benzylic alcohols in high yields, thereby expanding the substrate scope for future relevant cell assays.Graphical abstract

Synthesis, X-Ray Crystal Structures, and Preliminary Antiproliferative Activities of New s-Triazine-hydroxybenzylidene Hydrazone Derivatives

“…Similarly, s-triazine derivatives represent important class of compounds in medicinal chemistry [20][21][22][23]. Cyanuric chloride has been used as building blocks in the synthesis of vast derivatives bearing the s-triazine moiety, due to the low-cost, commercial availability, and ease of displacement of the three chlorine atoms by various nucleophiles under controlled temperature [24].…”

Synthesis, stability and printing properties of a novel 2‐sulphophenoxy‐4‐chloro‐s‐triazine reactive dye for ink‐jet printing of wool

“…Cyanuric chloride is an electron‐poor heterocycle with its reactive chlorine atoms easily substituted in nucleophilic aromatic substitution reactions. Furthermore, the reactivity of the remaining chlorine atoms depends upon the electrochemical character of the substitute and the positional relationship between the hetero‐nitrogen atoms and substituent …”