Synthesis of dibenzo[b,f][1,4]oxazepin-11(10H)-ones from 2-nitrobenzoic acids

Abstract

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.

Efficient Metal-Free Oxidative C–H Amination for Accessing Dibenzoxazepinones via μ-Oxo Hypervalent Iodine Catalysis

“…We Several synthetic methods have been developed to access dibenzoxazepinones. Among them, a widely employed approach involves a nucleophilic aromatic substitution reaction (Scheme 1, path a) [7][8][9]. According to previous reports, subjecting salicylamides and substituted benzenes to basic conditions triggers intermolecular nucleophilic aromatic substitution and sequential Smiles rearrangement, resulting in the formation of dibenzoxazepinones (Scheme 1, path b) [10][11][12][13].…”

Ni-Catalysed intramolecular reductive aminocarbonylation of 2-haloaryl-tethered nitroarenes for the synthesis of dibenzazepine-based heterocycles

“…In this context, Hu, 14 Wróbel, 15 and our group 16 developed cyclization methods via the intramolecular reductive coupling of ester (Scheme 1b, (i)) and benzoic acid (Scheme 1b, (ii)) tethered nitroarenes to the target dibenzoazepinone derivatives. Alternatively, the aromatic nitro group acts as the leaving group in the cyclization of the amide precursors to access the dibenzoazepinone derivatives 17 (Scheme 1b, (iii)).…”

Synthesis of dibenzo[b,f][1,4]oxazepin-11(10H)-one and pyrido[2,3-b][1,4]benzoxazepin-10(11H)-one compounds based on o-nitrochloro derivatives of benzene and pyridine

“…[7][8][9] This synthesis can be performed using different [10][11][12][13] esters 1a,b, and the cyclisation can be carried out in different solvents. [14][15][16] Another method for constructing the heterocyclic system of compounds 7a,b involves intramolecular aromatic substitution in 2-(o-halobenzamido)phenols, 2,4,17-19 2-(o-nitrobenzamido)phenols 2a 20,21 or 2-halo-N-(2-hydroxyphenyl)nicotinamides 2b. 4 Intramolecular acylation of 1-isocyanato-2-phenoxybenzenes 3 gives dibenzo[b,f] [1,4]oxazepin-11(10H)-ones 7a in good yields.…”