Synthesis of substituted 10,11-dihydro-5H-dibenz[b,f]azepines; Key synthons in syntheses of pharmaceutically active compounds

Substituted 10,11-dihydro-5H-dibenz[b,f]azepines are key synthons in the syntheses of a number of pharmaceutically active compounds such as imipramine, chlorimipramine, and desimipramine analogues. A facile synthesis of substituted 10,11-dihydro-5H-dibenz[b,f]azepines is described, starting out from...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 36; no. 1; pp. 57 - 64
Main Authors Jorgensen, TK, Andersen, KE, Lau, J, Madsen, P, Huusfeldt, PO
Format Journal Article
LanguageEnglish
Published ODESSA HETERO CORPORATION 01.01.1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Substituted 10,11-dihydro-5H-dibenz[b,f]azepines are key synthons in the syntheses of a number of pharmaceutically active compounds such as imipramine, chlorimipramine, and desimipramine analogues. A facile synthesis of substituted 10,11-dihydro-5H-dibenz[b,f]azepines is described, starting out from commercially available 2-bromotoluenes or 2-nitrotoluenes. Initial alpha-bromination with N-bromosuccinimide and subsequent reaction with triethylphosphite afforded the corresponding benzyl phosphonic ester derivatives. After reaction with benzaldehyde derivatives, the expected Horner-Emmons reaction products were obtained. Hydrogenation gave the amino derivatives which were transformed into the corresponding formamides. Under Goldberg conditions [1], the final ring closing step was performed to give the substituted 10,11-dihydro-5H-dibenz[b,f]azepines in 46-75% yield.
ISSN:0022-152X
DOI:10.1002/jhet.5570360110