135085-85-7Relevant academic research and scientific papers
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.
