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

doi:10.1002/JHET.5570360110

Paper

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

Published 1999 · T. K. Jørgensen, K. Andersen, J. Lau

Journal of Heterocyclic Chemistry

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Abstract

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 com mercially available 2-bromotoluenes or 2-nitrotoluenes. Initial α-bromination with N-bromosuccinimide and subsequent reaction with triethylphosphite afforded the corresponding benzyl phosphonic ester deriva tives. 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.

Study Snapshot

This study presents a facile synthesis of substituted 10,11-dihydro-5H-dibenz[b,f]azepines, key synthons in pharmaceutically active compounds, from readily available 2-bromotoluenes or 2-nitrotoluenes.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

A new method for bromination of carbazoles, β-carbolines and iminodibenzyls by use of N-bromosuccinimide and silica gel

N-bromosuccinimide and silica gel effectively bromate carbazoles, -carbolines, and iminodibenzyls in high yields at ambient temperature, while less selective brominations yield mixtures of products.

Citations

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