Issue 1, 1970

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

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.

Article information

Article type
Paper

J. Chem. Soc. C, 1970, 74-78

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

C. George, E. W. Gill and J. A. Hudson, J. Chem. Soc. C, 1970, 74 DOI: 10.1039/J39700000074

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