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

✍ Scribed by Daniel Obrecht; Bernhard Scholl; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
1985
Tongue
German
Weight
684 KB
Volume
68
Category
Article
ISSN
0018-019X

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✦ Synopsis

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).

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