111113-92-9Relevant academic research and scientific papers
A Light-Induced Unusual Synthesis of Substituted 3-Azaquinolizinones
Baum, Gerhard,Friderichs, Alois,Kuemmell, Andreas,Massa, Werner,Seitz, Gunther
, p. 411 - 416 (2007/10/02)
We describe the photochemical transformations of the cycloalkane-annulated pyridinium-N-aminides 8-10, which are conjugated with a benzylidene system.With 8, 1,3-electrocyclisation takes place leading to the cyclopenta-1,2-diazepine 25 via the diazanorcaradiene 12 which subsequently underwent valence tautomerisation.Contrary to 8, with 9 and 10, 1,5-electrocyclisation is dominating yielding 14 and 15 as nonisolable intermediates; these rearrange in a rationalized reaction sequence e.g. 29 -> 30a 30b -> 26 to give the novel 3-azaquinolizinones 26 and 27, respectively.The structure of 27 is proven by X-ray diffraction.
