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REVISTA DE CHIMIE
Cite as: Rev. Chim.
https://doi.org/10.37358/Rev.Chim.1949

OSIM Nr. R102355
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Revista de Chimie (Rev. Chim.), Year 2007, Volume 58, Issue 2,





Synthesis and Characterization of Some New
2-Methyl-O-Acyl-Oximino-DibenzOxepins

Abstract:

This paper is a continuation of our research and presents the chemical modeling that we made on the dibenz[b,e]oxepinic system, with the aim of obtaining new compounds with potential antidepressive action, that contain in the same molecule two pharmacologically active elements: the dibenzoxepin system and the oximinic group. For the new compounds synthesized, we used as intermediate substance 2-methyl-6,11-dihydro-dibenz[b,e]oxepin-11(6H)-one, prepared by cyclizing the 2-(4-methyl-phenoxymethyl)-benzoic acid (which resulted from phtalide and potassium p-cresolate). After treating the aforementioned ketone with hydroxylamine hydrochloride, we obtained 2-methyl-11-hydroxyimino-6,11-dihydro-dibenz[b,e]oxepin. This oxime was acylated with different substituted benzoic acid chlorides and we obtained the 2-methyl-O-acyl-oximino-dibenz[b,e]oxepins. We established the optimal reaction conditions to synthesize the new compounds with high purity and yields. The new compounds, which have not been mentioned in the literature concerning this domain, have been characterized by their physical constants (melting point, solubility), structurally by NMR, IR analysis and by elemental analysis. To obtain new compounds from the dibenz[b,e]oxepin series with potential pharmacological action, we synthesized eight new 2-methyl-O-acyl-oximino-dibenz[b,e]oxepins. The spectral and elemental analysis confirmed the final and intermediate compounds structures and also the synthesis that we had done. Keywords: dibenz[b,e]oxepin, 1H-NMR, 13C-NMR

Issue: 2007, Volume 58, Issue 2
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