Collect. Czech. Chem. Commun. 2009, 74, 1137-1150
Published online 2009-07-17 23:59:42

Some acid-catalysed reactions of indol-3-yl and indol-2-yl disubstituted methanols

Mardi Santoso, Naresh Kumar and David StClair Black*

School of Chemistry, The University of New South Wales, UNSW Sydney, NSW 2052, Australia


1-Substituted indol-3-yl and indol-2-yl disubstituted methanols do not undergo acid-catalysed trimerisation to yield indolocyclotriveratrylenes, unlike the related primary 1-substituted indol-3-yl- and -2-ylmethanols. The 1-substituted indol-3-ylmethanols 10 and 11 gave diindol-3-ylmethanes 12 and 13, respectively, on treatment with p-toluenesulfonic acid in dichloromethane. In contrast, the indol-2-ylmethanols 22 and 23 gave the reduced indolo[3,2-b]carbazoles 24 and 25, respectively, on treatment with boron trifluoride etherate in benzene. An X-ray crystal structure of compound 24 is described.

Keywords: Indoles; Diindol-3-ylmethanes; Indolocarbazoles; Acid-catalysed addition reactions; Isatins; Ketone reduction.

References: 19 live references.