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Synthesis of 7‐substituted 1 H ‐indolo[3,2‐ d ][1,2]benzoxazepines
Author(s) -
Klioze Sol S.,
Ehrgott Frederick J.,
Glamkowski Edward J.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210502
Subject(s) - chemistry , sodium hydride , ring (chemistry) , indole test , intramolecular force , ketone , stereochemistry , d 1 , medicinal chemistry , organic chemistry , biochemistry , receptor
The synthesis of the novel 7‐substituted 1 H ‐indolo[3,2‐ d ][1,2]benzoxazepine ring system is described. Fischer indolization of 2‐fluoroacetophenone phenylhydrazone provided the starting material 2‐(2‐fluorophenyl)‐1 H ‐indole. An acyl group was then introduced at the 3‐position of the indole nucleus and the resulting ketone was converted to the ketoxime. Upon treatment with sodium hydride to form the oxanion of the ketoxime, an intramolecular cyclization took place via displacement of fluoride from the adjacent 2‐fluorophenylsubstituent. This ring closure completed the construction of the 1 H ‐indolo[3,2‐ d ][1,2]benzoxazepine ring system.