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

Synthesis of 3,3‐Dimethylperhydro‐1,4‐diazepin‐2,5,7‐triones from 3‐Dimethylamino‐2,2‐dimethyl‐2 H ‐azirine and Malonic Acid Monoamides Reaction of the aminoazirine 1 and malonic acid monoamides 5 in CH 3 CN 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 CH 3 CN 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°. It has been shown that 2‐oxazolin‐5‐ones are intermediates in the selective cleavage of the therminal amide function of 6 ( Scheme 3 ).