A new strategy to 2-aminochromanes through catalyst-free cascade reaction of 3-trifluoroacetyl-4H-chromenes and 4H-chromene-3-carbaldehydes with cyclic secondary amines is presented. The reaction proceeds through subsequent 1,4- and 1,2-additions of amine, bimolecular elimination of trifluoroacetamide or formamide, and 6-exo-trig cyclization. The latter stage is a very rare example of addition of phenols to enamines. The obtained semicyclic N,O-acetals were applied as useful precursors for the synthesis of other chromanes.
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