Reaction of diazoalkanes with 4-substituted 1,2,4-triazole-3,5(4H)-diones

Abstract

Diazoacetic esters reacted with 4-substituted 1,2,4-triazole-3,5(4H)-diones (2) to give one-to-one adducts. Molecular weight determination, high-performance liquid chromatography, and 2D n.m.r. spectroscopy showed that the adducts are monomers that associate in solution. The monomers are most likely 1,3,5-trizabicyclo[3.1.0]hexane-2,4-diones. The adducts were thermally isomerized to 3,6-disubstituted 1,3,5-triazine-2,4(1H,3H)-diones. Diphenyldiazomethane reacted with (2) to yield an azomethine imine, which underwent thermal dimerization followed by rearrangement.