88366-03-4Relevant academic research and scientific papers
Fragmentation Reactions of N-Acyldienamines Giving Conjugated Enimines
Kiehl, Georges,Streith, Jacques,Tschamber, Theophile
, p. 2141 - 2150 (2007/10/02)
Azetidinodiazepines 1 and 2, when heated up to 200 deg C, lead to the enimines 5 and 6, respectively.The mechanism of this fragmentation was elucidated via thermolysis of the educts 8 and 10.The first one gives the enimine 5 and N-methylurethane 9 when heated in methanol.The second one gives the doubly-deuterated enimine 13, a result which shows that the N-deuteriodienamine 11 is a short-lived intermediate leading, via a many-stage prototropy, to the final enimine.Benzoylazetidinodiazepines 16 and 18, when heated in trifluoroacetic acid, lead in a similar way to the corresponding enimines 17 and 19, respectively, as well as to benzoic acid.Ammonolysis of the azetidinodiazepines 21 and 23 leads not only to the cleavage of the carbamoyl group but also to ring-opening of the β-lactam ring with formation of the dihydrodiazepines 22 and 24.Similarly, ammonolysis of the monocyclic educt 28 gives the enimine 29.
