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The reaction of equimolecular quantities of a nitrile and triflic anhydride or triflic acid at low temperature produce an intermediary nitrilium salt that consequently reacts with 2 equiv of a various nitrile at greater temperature to form 2,4-disusbstituted-6-substituted 1,3,5-triazines in middle to great yields. This fabricated procedure has also been applied to the ready of a 1,3,5-triazine having actually three various substituents. The outcomes are described in terms of a mechanism based upon the relative stability that the intermediate nitrilium salts the are formed through a reversible pathway. The formation of a substituted isoquinoline making use of benzyl cyanide together the second nitrile support the postulated mechanism and also the framework of derivatives of the proposed intermediate when the reaction is brought out in the visibility of different nucleophiles other than nitriles. Theoretical calculations and the monitoring of the reaction making use of 1H and also 13C NMR spectroscopy space in commitment with the proposed system pathway.
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IR, 1H NMR and 13C NMR spectra (1D and also 2D), crystallographic data because that 3c, consisting of CIF files, also the Cartesian coordinates and also total energies of all the stationary points disputed in the manuscript. This material is available free of fee via the web at http://thedesigningfairy.com.