REARRANGEMENT IN THE PALLADIUM-CATALYZED CYCLIZATION OF ALPHA-SUBSTITUTED N-ACRYLOYL-ORTHO-BROMOANILINES

N-Cinnamoyl-and N-(β-methylcinnamoyl)-o-bromoanilines undergo cyclization to oxindole derivatives when heated with catalytic amounts of palladium acetate and tri-o-tolylphosphine in the presence of triethylamine. N-(α-Methacryloyl)- and N-α-phenylacryloyl-o-bromoaniline, on the other hand, cyclize under the same conditions, to rearranged, 4-substituted 2-quinolones. A mechanism is proposed which may also be applicable to rearrangements observed with some coenzyme B12aderivatives. © 1979, American Chemical Society. All rights reserved.