Indoles from 3-nitropyridinium salts 9. Methyl ethyl ketone N-methylimine in the indolization of 1-methyl-3-nitropyridinium salts

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In a study of the direction of the indolization of alkyl-substituted 3-nitropyridinium salts in reaction with methyl ethyl ketone N-methylimine as a function of the structure of the salts, it has been established that in the presence of a substituent at position 4, initial attack at position 6 by the most substituted enamine form of the imine leads to preferential formation of 7-methylindole whereas in its absence the regioselectivity of the process is reduced and in the indole mixture the fraction of 3-methylindole increases.