[Reaction: see text]. 1,3-dinitrodibenz[b,f][1,4]oxazepin-11(10H)-one, prepared by intramolecular displacement of nitro group in N-(2-hydroxyphenyl)-2,4,6-trinitrobenzamide, reacts with O- and S-nucleophiles to yield the products of mono- or bis-substitution of the nitro groups. The nitro group in position 3 is displaced first. This observation is in contrast with earlier results for the nitro-substituted benzoannulated five-membered heterocycles. This difference in reactivity is likely due to the increased steric hindrance for peri-nitro group displacement in the case of the benzoannulated seven-membered heterocycle. N-Alkylation of the nitro-substituted dibenz[b,f][1,4]oxazepin-11(10H)-ones yields analogues of a known antidepressant drug Sintamil. The structure of the products is confirmed by NOE experiments and alternative synthesis.
1,3 Dinitro[b,f]dibenzoxepine undergoes nucleophilic substitution with O and S nucleo philes, the nitro group at position 1 (peri nitro group) being selectively replaced. The factors responsible for the selectivity of the reaction are discussed.
Base catalyzed intramolecular nucleophilic substitution for the 2 nitro group in 2 hydr oxyanilides of 2 nitrobenzoic acids gave dibenzo[b,f ][1,4]oxazepin 11(10H ) ones. In particu lar, 3 nitrodibenzo[b,f ][1,4]oxazepin 11(10H ) one was obtained from N (2 hydroxyphenyl) 2,4 dinitrobenzamide. The nitro group in the product could also be replaced under the action of O and S nucleophiles.
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