Collect. Czech. Chem. Commun. 1982, 47, 65-71

Antidepressant fluorinated prothiadene derivatives: 9-Fluoro and 2,9-difluoro derivative of 11-(3-dimethylaminopropylidene)-6,11-dihydrodibenzo[b,e]thiepin

Miroslav Rajšner, Emil Svátek, Jan Metyš and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


6-Fluorophthalide (IV), obtained from 6-aminophthalide by the Schiemann method, was transformed by reactions with potassium salts of thiophenol and 4-fluorothiophenol and 4-fluorothiophenol to the acid V and VI. Cyclization with polyphosphoric acid gave 9-fluoro- and 2,9-difluorodibenzo[b,e] thiepin-11(6H)-one (VII, VIII) which were treated with 3-dimethylaminopropylmagnesium chloride and afforded the tertiary alcohols IX and X. Dehydration by heating with dilute hydrochloric acid resulted in the title compounds II and III whose IR spectra indicated the E-configuration. Both compounds showed properties of tricyclic antidepressants being, however, less active than prothiadene (I) in the tests for the antireserpine activity.