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8110989 
Journal Article 
New Psychotropic Agents. III. Derivatives of 6,11-Dihydrodibenz[b,e]oxepine and 6,11-Dihydrodibenzo[b,e]thiepine 
Wixthrop, SO; Davis, MA; Herr, F; Stewart, J; Gaudry, R 
1962 
5 
6 
1207-1215 
English 
Cyclodehydrations were carried out successfully on 2-carboxybenzyl phenyl ether (IVa), 2-carboxybenzyl 4-chlorophenyl ether and 2-carboxybenzyl phenyl thioether (IVb) to yield, respectively, 11-keto-6,11-dihydrodibenz[b,e]oxepine (Va), 2-chloro-11-keto-6,11-dihydrodibenz[b,e]oxepine and 11-keto-6,11-dihydrodibenzo[b,e]thiepine (Vb). Alkylation with 3-dimethylaminopropylmagnesium chloride gave the somewhat unstable 11-(3-dimethylaminopropyl)-11-hydroxy compounds which under dehydrating conditions unexpectedly rearranged to anthracene-like products. In contrast, 11-keto-6,11-dihydrodibenzo[b,e]-thiepine-5,5-dioxide (Vc) produced an 11-(3-dimethylaminopropyl)-11-hydroxy compound (Vic) which underwent dehydration without rearrangement and yielded the expected olefin (VII). The pharmacological activity of this latter compound is discussed briefly. © 1962, American Chemical Society. All rights reserved.