95793-10-5Relevant academic research and scientific papers
Preparation of Alkyl Substituted 1,3,4-Oxadiazin-6-ones by the DCC Induced Cyclization of 2-Oxoalkanoic Acid Acylhydrazones
Padwa, Albert,Eisenbarth, Philipp
, p. 61 - 64 (2007/10/02)
A series of 2,5-disubstituted 1,3,4-oxadiazin-6-ones were prepared by treating syn-2-oxoalkanoic acid acylhydrazones with dicyclohexylcarbodiimide.The isomeric anti isomers produced acylureas when treated with DCC.The cycloaddition reaction of 5-methyl-2-phenyl-1,3,4-oxadiazin-6-one with norbornene was studied and found to give a nitrogen deficient 1:1-cycloadduct.The formation of the product can be rationalized in terms of a Diels-Alder cycloaddition followed by nitrogen extrusion and cyclization of the resulting γ-ketoketene intermediate.
