Synthese von 3,3-Dimethylperhydro-1,4-diazepin-2,5,7-trionen aus 3-Dimethylamino-2,2-dimethyl-2H-azirin und Malonsaeuremonoamiden

Article abstract of DOI:10.1002/hlca.19850680220

Synthesis of 3,3-Dimethylperhydro-1,4-diazepin-2,5,7-triones from 3-Dimethylamino-2,2-dimethyl-2H-azirine and Malonic Acid Monoamides.Reaction of aminoazirine 1 and malonic acid monoamides 5 in CH3CN yielded triamides of type 6 (Scheme 2), which were transformed to the corresponding phenylthioates 9 by treatment of a solution of 6 and thiophenol in CH3CN with HCl (Scheme 4).Cyclization of 9 to give the 1,4-diazepin-2,5,7-trione of type 10 was achieved with NaH in toluene at about 90 deg.It has been shown that 2-oxazolin-5-ones are intermediates in the selective cleavage of the therminal amide function of 6 (Scheme 3).