• The first stage of this reaction, to start the formation of the reagent for the second half, goes by an E1 mechanism.
  • The reagent for the conjugate addition step which has been formed in the first part of the reaction is called acrolein.
  • In the second half of the reaction a conjugate addition begins the mechanism. The first half simply forms the reagent.
  • Ring closure comes from an electrophilic aromatic substitution reaction. This is followed by an E2 elimination.
  • The reagent for the loss of H2 at the end of the reaction is PhNO2.
  • Isoquinoline can be formed by the Bischler-Napieralski reaction.
  • An alternative reaction mechanism for the Skraup process is called the Doebner-Von Miller reagaction. It goes via an intermolecular [2+2] cycloaddition.


    References:
  • Theoclitou M-E.; Robinson L.A.; Tetrahedron Letters, 2002, Volume 43, Issue 21, 3907-3910
  • O'Neill P.M.; Storr R.C.; Park B.K.; Tetrahedron, 1998, Volume 54, Issue 18, 4615-4622