UNTERSUCHUNGEN AN DIAZOVERBINDUNGEN UND AZIDEN-LIII. ABFANGREAKTIONEN INSTABILER AZOMETHINIMIN-DIPOLE MIT ETHANOL

Article abstract of DOI:10.1016/S0040-4020(01)96561-5

The reaction of the diazo compounds 1a-o with 4-phenyl-1,2,4-triazolin-3,5-dione (2) in dichloromethane-ethanol leads to the urazoles 5a-o; they arise from the primarily formed unstable azomethinimine dipoles 4a-o by ethanol addition.Acidic hydrolysis of 5k and 5o yields the α-diketones 8 and 10 besides 4-phenyl urazole (9).Bistriazolindinones (13a,b) react analogously with diazo compounds (1l, m) in the presence of ethanol to give the bisurazoles 14a-c.