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Synthese von 3,3‐Dimethylperhydro‐1,4‐diazepin‐2,5,7‐trionen aus 3‐Dimethylamino‐2,2‐dimethyl‐2 H ‐azirin und Malonsäuremonoamiden
Author(s) -
Obrecht Daniel,
Scholl Bernhard,
Heimgartner Heinz
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680220
Subject(s) - chemistry , thiophenol , malonic acid , azirine , amide , toluene , medicinal chemistry , organic chemistry , ring (chemistry)
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 ).