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

Abstract

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