REACTION OF SECONDARY CROSS-CONJUGATED KETO ENAMINES WITH ACYL ARYL DIAZENES

The reaction of some secondary cyclic alpha-ketoenamines with electrop hilic diazenes of the type Ar-N=N-COAr1 has been investigated. Aromati c alpha-ketoenamines reacted with diazenes to afford the relevant 1,3, 4-oxadiazine derivatives, whereas aliphatic alpha-ketoenamines, under the same conditions, directly the more stable ketoenamine adducts. 1,3 ,4-oxadiazines, when heated in the presence of a catalytic amount of T sOH, underwent ring opening, providing both addition and rearrangement products by independent pathways. A possible mechanism for the format ion of these latter compounds is proposed.