Synthesis of Genotoxic Heterocyclic Amines Trp-P-1 and Trp-P-2

Article abstract of DOI:10.1021/jo00048a026

Trp-P-1 (1a) and Trp-P-2 (1b) possessing a pyrido<4,3-b>indole system have been newly synthesized.The key reaction step in the synthetic sequence has been the thermal electrocyclic reaction of the 1-azahexa-1,3,5-triene system 3 involving the indole bond derived from 2-vinylindoles 4. 2-Vinylindole 4a has been derived from N-(benzenesulfonyl)indole (5) in a four-step sequence. 2-Vinylindole 4b has been synthesized by two routes using either ethoxymethylidene Meldrum's acid (6b) or diethyl ethoxymethylidenemalonate (10) as Michael acceptors to the 2-lithio-N-(benzenesulfonyl)indole.