Synthese von 3,3-Dimethylperhydro-1,4-diazepin-2,5,7-trionen aus 3-Dimethylamino-2,2-dimethyl-2H-azirin und Malonsäuremonoamiden |
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Authors: | Daniel Obrecht Bernhard Scholl Heinz Heimgartner |
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Abstract: | 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 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). |
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