Tetrahedron

N-Acylated α-aminonitriles and their conversion into 5-aminooxazole, 5 (4h)-oxazolone and 4 (5h)-imidazolone derivatives

P Verschave, J Vekemans, G Hoornaert

Index: Verschave, P.; Vekemans, J.; Hoornaert, G. Tetrahedron, 1984 , vol. 40, # 12 p. 2395 - 2404

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Citation Number: 19

Abstract

In contrast with the reaction of α-aminonitriles 1 a, the corresponding N-acylated α- aminonitriles 1 bf and oxalyl chloride do not yield pyrazinone derivatives, but 5- aminooxazoles 9-11 or 4 (5H)-imidazolones 12, the latter being converted in some cases into imidazo [2, 1-a] isoquinoline-2, 5, 6 (3H)-triones. Reactions of compounds 1 bf and ethyl chlorooxoacetate provide evidence for a 5 (4H)-iminooxazole intermediate 7, which ...