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We report a general protocol for the direct N-allylation of electron-poor N-heterocyclic amides and sulfonamides via an amide-aldehyde-alkene condensation reaction catalyzed by a Lewis acid. This process has a broad substrate scope with respect to N-heterocyclic amides including carbamates, carboxamides, and N-methylsulfonamides, and provides efficient access to a variety of allylamine derivatives in good yield with high regioselectivity. The utility of this method was also demonstrated by the rapid synthesis of Naftifine from N-methyl-1-naphthamide, paraformaldehyde, and styrene in one-pot.

The allylation reaction proceeds with high regioselectivity and has a broad substrate scope.

The title reactions afford regioselectivity N3- or N1-alkylated quinazolinone derivatives (III) or (V), resp., depending on the steric bulk of the aryl groups.