Collect. Czech. Chem. Commun. 1980, 45, 517-528

Carbamates and ureas derived from 11-amino-6,11-dihydrodibenzo[b,e]thiepin; Synthesis and pharmacological screening

Vladimír Valenta, Marie Bartošová and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 00 Prague 3


A series of N-substituted carbamates V-XIII was prepared by reactions of 6,11-dihydrodibenzo[b,e]thiepin-11-ol (I) with carbamates H2NCOOR in acetic acid. Whereas the Leuckart reaction of dibenzo[b,e]thiepin-11(6H)-one yielded 9-formamido-10-methylene-9,10-dihydroanthracene (XVIII), a satisfactory method for preparing the amine III was found in heating the carbamate V with 2-aminoethanol to 170°C. Reactions of the amine III with isocyanates gave most of the disubstituted ureas XX-XXV. The expected anticonvulsant activity was found only in high doses with compounds IX, XII, XV, XX, XXI and XXXIII.