Romanian Society of Pharmaceutical Sciences

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SYNTHESIS AND STRUCTURE ELUCIDATION OF SOME NEW O-ACYL-OXIMINODIBENZO[ b,e]THIEPINES AND O-ACYLOXIMINO- DIBENZO[b,e]THIEPINE-5,5- DIOXIDES

CAMELIA ELENA STECOZA1*, CORINA ILIE2, CONSTANTIN DRĂGHICI3, MIRON TEODOR CĂPROIU3

1University of Medicine and Pharmacy “Carol Davila” Bucharest, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 6 Traian Vuia, 020956, Bucharest, Romania
2National Institute for Chemical Pharmaceutical R&D – ICCF, Vitan Avenue 112; Bucharest, Romania
3Center of Organic Chemistry „C.D. Nenitescu”, Romanian Academy, 202 B Splaiul Independenţei, 060023, Bucharest, Romania

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The aim of the present paper was the synthesis and characterization of some new dibenzo[b,e]thiepine derivatives. O-acyl-oximino-dibenzo[b,e]thiepines (3) were obtained by acylation of 11-hydroximino-6,11-dihydro-dibenzo[b,e]thiepine (2) with various acid chlorides. O-acyl-oximino-dibenzo[b,e]thiepine-5,5-dioxides (4) were synthesized using two different pathways. Thus, compounds 4a-b have resulted by oxidation of O-acyloximino- dibenzo[b,e]thiepines 3a-b and compounds 4c-f have resulted following a multistage synthesis which implies transforming the 6,11-dihydrodibenzo[b,e]thiepin- 11(6H)-one (1) into the corresponding 5,5-dioxide (5) and subsequently to the corresponding oxime (6), the acylation taking place in the last stage. All the new products were characterized by their physical properties, and the structures were confirmed by elemental analysis and spectral analysis (1H-NMR, 13C-NMR, IR).