Synthesis of 2, 4-Diamino-6, 7-dihydroimidazo[1, 2-a] [1, 3, 5]triazine Derivatives

Abstract

While reaction of 2-chloro-4-(2-hydroxyethylamino)-6-(p-toluidino)-1, 3, 5-triazine [ 5 ] with p-toluidine gave normal aromatic nucleophilic substitution product 2-(2-hydroxyethylamino)4, 6-di(p-toluidino)-1, 3, 5-triazine [ 8 ], 2-arylamino-4-chloro-6-(2-chloroethylamino)-1, 3, 5triazines, [ 3 ] and [ 4 ], with arylamines at 110°C gave 2, 4-diamino-6, 7-dihydroimidazo [1, 2-a] [1, 3, 5] triazine derivatives, [ 6 ] and [ 7 ] respectively, in good yields.
These novel bicyclic heterocyclic compounds are probably formed through aromatic nucleophilic substitution followed by intramolecular cyclization. IR, ¹H-NMR and ¹³C-NMR spectral data of [ 6 ] and [ 7 ] are discussed.