The rearrangement of N-(2-bromoallyl)-arylamines to 2-methylindoles.

doi:10.1039/J39700000074

Paper

The rearrangement of N-(2-bromoallyl)-arylamines to 2-methylindoles.

Published 1970 · C. George, E. Gill, J. Hudson

Journal of the Chemical Society. Perkin transactions 1

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3

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Abstract

N-(2-Bromoallyl)-arylamines cyclise readily to substituted 2-methylindoles when heated with methanolic or aqueous boron trifluoride. Methyl, hydroxy-, and halogeno-substituted 2-methylindoles can be prepared in very good yield by this procedure. The reaction was shown to be intramolecular and two possible mechanisms are discussed : (i) a Claisen rearrangement and (ii) a mechanism involving a concerted bromine elimination and 1,2-nitrogen shift to give an allylic carbonium ion, followed by ring closure. Experiments with carbon-14 labelled N-2-bromoallylaniline gave an isotope distribution in the product midway between that expected for either of these mechanisms.

Study Snapshot

This study demonstrates that N-(2-bromoallyl)-arylamines readily cyclize to substituted 2-methylindoles when heated with boron trifluoride, with two possible mechanisms: Claisen rearrangement and concerted bromine elimination and 1,2-nitrogen shift.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

The rearrangement of N-(2-bromoallyl)-arylamines to 2-methylindoles.

References

Citations

The stereochemistry of N-methyl and aryl substituents determine the biological activities of 3-aryl-8-methyl-8-azabicyclo[3.2.1]oct-2,3-enes.

The biological activities of aryl-substituted tropanes are strongly correlated with the nature and orientation of the aryl group, as well as the relative orientation of the N-methyl group.