Abstract
In contrast with the reaction of α-aminonitriles 1 a, the corresponding N -acylated α-aminonitriles 1 b-f and oxalyl chloride do not yield pyrazinone derivatives, but 5-aminooxazoles 9 - 11 or 4(5 H )-imidazolones 12 , the latter being converted in some cases into imidazo [2,1- a ]isoquinoline-2,5,6(3 H )-triones. Reactions of compounds 1 b-f and ethyl chlorooxoacetate provide evidence for a 5(4 H )-iminooxazole intermediate 7 , which aromatizes to yield 5-aminooxazoles 9 - 11 ; however, unaromatizable īntermediates of type 7 - isolable as 5(4 H )y-oxazolones 13 after hydrolysis - undergo a catalyzed Dimroth-type rearrangement to give imidazolone derivatives 12 .
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