178875-20-2Relevant academic research and scientific papers
REACTION OF SECONDARY CROSS-CONJUGATED KETO ENAMINES WITH ACYL ARYL DIAZENES
Felluga, Fulvia,Nitti, Patrizia,Pizzioli, Alessandro,Prodan, Massimo,Russo, Claudio
, p. 297 - 302 (2007/10/03)
The reaction of some secondary cyclic α-ketoenamines with electrophilic diazenes of the type Ar-N=N-COAr1 has been investigated.Aromatic α-ketoenamines reacted with diazenes to afford the relevant 1,3,4-oxadiazine derivatives, whereas aliphatic α-ketoenamines, under the same conditions, gave directly the more stable ketoenamine adducts. 1,3,4-Oxadiazines, when heated in the presence of a catalytic amount of TsOH, underwent ring opening, providing both addition and rearrangement products by independent pathways.A possible mechanism for the formation of these latter compounds is proposed.
