22928-91-2Relevant articles and documents
Stereospecific Synthesis of 2-Oxazinyl-4-oxoazetidinecarbamates Starting from a 1,2-Diazephine. A New Type of Intramolecular Transbenzoylation
Fritz, Hans,Henlin, Jean-Michel,Riesen, Andreas,Tschamber, Theophile,Zehnder, Margareta,Streith, Jacques
, p. 822 - 834 (1988)
Azetidinodiazepines 4b and 4c react with acylnitroso dienophiles 5a-c, specifically from their convexe α-side, but in a non-regiospecific way, leading thereby stereospecifically to the expected adducts 6a-d and 7a-d.The three-dimensional structures of 6a and 7a were determined by X-ray analyses which corroborated their NMR data.OsO4 cis-glycolization occured in good yield with the inverse adducts 7a and 7e and led to the rearranged products 10.These latter ones result from an intramolecular N- to O-transbenzoylation of the short-lived intermediates 9 followed by fragmentation of the aminal function.X-Ray analysis of 7a showed the N(10) atom to be pyramidal, a result which demonstrates that it does not have any pronounced benzamide character; otherwise no such N- to O-transbenzoylation would have taken place.Structure and relative configuration of 10a were ascertained by X-ray analysis which confirmed its NMR data as well as the stereochemical outcome of its formation.
Studies on diazepines. XVI. Synthesis of monocyclic 1,3-diazepines. (1). Thermolysis of 1,2-diazepines formed from methylpyridine N-imides
Kurita,Kojima,Tsuchiya
, p. 3688 - 3695 (2007/10/02)
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