Construction of 1,2-dihydro-1,3,5-triazines via reactions involving amidines

1,2-Dihydro-1,3,5-triazine compounds were synthesized through three sets of reactions of amidines with, respectively, paraformaldehyde, aldehydes and N-arylnitrones under different conditions. The catalysts used in these three reactions were Cu(OAc)₂, ZnI₂ and CuCl₂·2H₂O, respectively. Most of the substrates tested for these reactions provided the target products in moderate to good yields. In the reactions involving paraformaldehyde, Cu(OAc)₂ also accelerated the release of formaldehyde from paraformaldehyde during the catalytic reaction process. In the case of the reactions involving nitrones, CuCl₂·2H₂O not only catalyzed the normal progress of the main reaction, but also promoted the reaction of nitrones to produce nitroso compounds and aldehydes.