Tetrahedron p. 2919 - 2922 (1985)
Update date:2022-08-12
Topics:
Dunsdon
Martin
The structures of doxepin and serotonin were overlayed using molecular graphics and 1-[2-(dimethylamino)ethyl]-7,12-dihydro-3H-[2]-benzoxepino[4,3-e]indole was proposed as a potential antidepressant agent. This paper deals with the synthesis of the title compound. Key steps in the synthesis include a regioselective electrophilic substitution at C-4 of ethyl 5-hydroxy-1-indolecarboxylate and subsequent modification to 7,12-dihydro-3H-[2]-benzoxepino[4,3-e]indole. Standard procedures were then used to construct the dimethylaminoethyl side chain to yield the title compound.
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Doi:10.1021/ja01270a037
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