135212-89-4Relevant academic research and scientific papers
5ar-p-Tolyl-6at,7t,8,9,10t,10at-hexahydro-11H,13H-7,10-methanobenzoxazino-benzoxazin-13-one
Kapor, Agnes,Stajer, Geza,Frimpong-Manso, Samuel,Bernath, Gabor
, p. 131 - 134 (1995)
The structure of the pentacyclic title compound, C23H23NO3, was established by X-ray diffraction.The exo positions of the aryl group, indicated by the NMR data, were confirmed by the relevant torsion angles: C11-O10-C2-C19 = -79.7 (3), C4-N3-C2-C19 = -98.5 (3) and C13-N3-C2-C19 = 86.2 (4) deg.The position of the aryl group is stabilized by a C24-H24...N3 interaction ...N3 2.480 (2), C24...N3 2.855 (4) Angstroem, C24-H24...N3 98.7 (2) deg>.The conformations of the benzoxazine rings I and II are twist-boat (1T3) and screw-boat (1S6), respectively.
Preparation of Diastereomeric 5,8-Methanobenzoxazino- and -1,3-benzoxazin-4-ones by Reaction of Norbornane/ene-condensed Dihydro-1,3-oxazines with Salicyl Chloride
Stajer, Geza,Frimpong-Manso, Samuel,Bernath, Gabor,Sohar, Pal
, p. 753 - 757 (2007/10/02)
Norbornane and norbornene-condensed dihydro-1,3-oxazines 1-6 were converted with salicyl chloride to 5,8-methanobenzoxazino- and --1,3-benzoxazin-4-ones 7-12.The addition takes place to the C=N bond: after acylation, the intermediate is stabilized through cyclization to the aryl-substituted carbon by hydrogen chloride elimination.Diastereomers containing the oxazine rings in isomeric positions could be isolated in two cases.This is the first example of the isolation of diastereomers in such a salicyl chloride reaction.In contrast with earlier findings with reactions of related systems, no addition to the C=C bond could be observed.The steric structures of the compounds were elucidated by ir, 1H- and 13C-nmr spectroscopy.
