Synthesis of genotoxic heterocyclic amines Trp-P-1 and Trp-P-2

The synthesis of the 3-amino-1,4-dimethyl and 3-amino-1-methyl derivatives of 5H-pyrido(4,3-b)indole (Trp-P-1 and Trp-P-2) proceeds through the thermal electrocyclic reaction of the 1-azahexa-1,3,5-triene system involving the indole (b) bond. N-(benzenesulfonyl)indole provides the 2-vinylindole substrates via a four-step sequence. Trp-P-1 and Trp-P-2 are genotoxic heterocyclic amines produced by the overcooking of protein-containing food.