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Novel synthesis of 2 H ‐3,1‐benzoxazine derivatives
Author(s) -
Li JiaRong,
Ma ShuLing,
Sun YongJiang,
Wei XiaoJie,
Zhou ZhiMing
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430332
Subject(s) - chemistry , cyclohexanone , cyclopentanone , imine , crystal structure , elemental analysis , proton nmr , catalysis , yield (engineering) , single crystal , nmr spectra database , crystallography , organic chemistry , stereochemistry , medicinal chemistry , spectral line , materials science , physics , astronomy , metallurgy
AbstractOn heating of the 2‐amino‐5‐nitrobenzonitrile 1 with cyclohexanone 2a in the presence of catalyst, the novel compound 6‐nitrospiro[3,1‐benzoxazine‐2,1′‐cyclohexan]‐4(1 H )‐imine 5a was formed. Also, reaction of 1 with cyclopentanone 2b or cycloheptanone 2c afforded 5b or 5c respectively. All new compounds were identified by 1 H NMR, 13 C NMR, IR, MS spectra and elemental analysis. The crystal structure of product 5a was determined by crystal X‐ray diffraction. And the mechanism for these reactions is proposed.