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Note | Regular issue | Vol 51, No. 1, 1999, pp.185-189
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8369
■ Mechanistic Insight into the Aromatization of Cyclic p-Quinonemethides to Indoles

Tushar A. Kshirsagar* and Laurence H. Hurley

*c/o Business Office PHR 5.114, College of Pharmacy, The University of Texas at Austin, Austin, Texas 78712-1074, U.S.A.

Abstract

Two mechanisms have been previously proposed for the aromatization of cyclic p-quinonemethides to indoles. A novel synthetic route to indoles via an unstable cyclic p-quinonemethide has provided additional insight into the mechanism of cyclization. Since this key intermediate lacks the functional groups required for one of the mechanistic pathways (Pathway B), it appears that cyclization occurs via Pathway A.