Synthesis and structure of azido-and amino-substituted dibenzoxazepinones |
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| Authors: | A V Samet K A Kislyi V N Marshalkin Yu A Strelenko Yu V Nelyubina K A Lyssenko V V Semenova |
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| Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation;(2) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation |
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| Abstract: | 1,3-Dinitrob, f]1,4]dibenzoxazepin-11(10H)-one enters nucleophilic substitution reactions with N-nucleophiles, azide ion preferably replacing the nitro group in position
3, whereas amines the one in position 1. Structures of the substitution products were confirmed by X-ray diffraction and 1H NMR NOE spectroscopy. The selectivity observed in the reaction with amines was supposed to be caused by the stabilization
of the intermediate σ-complex with the NH…O intramolecular hydrogen bond.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2018–2022, October, 2007. |
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| Keywords: | dibenz[b f][1 4]oxazepinones SNAr substitution reaction aromatic nitro compounds arylazides arylamines |
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