141734-67-0Relevant articles and documents
Synthesis of 3,4-Bridged Indoles by Photocyclisation Reactions. Part 1. Photocyclisation of Halogenoacetyl Tryptophan Derivatives
Beck, Anthony L.,Mascal, Mark,Moody, Christopher J.,Slawin, Alexandra M. Z.,Williams, David J.,Coates, William J.
, p. 797 - 812 (2007/10/02)
Although irradiation of N-chloroacetyltryptophan results in a poor yield of photocyclisation to the indole 4-position due to competing cyclisation to C-2, the photocyclisation of (dichloroacetyl)tryptophan derivatives gives, after addition of a nucleophile in work-up, 7-substituted pyrrolobenzazocines in good yield and with trans-stereospecificity.N-(Trichloroacetyl)tryptophan derivatives also undergo photocyclisation to give 3,4-bridged indoles.The structures of the azocinoindoles 13, 21, 22 and 35, and the azepinoindole 15 were confirmed by X-ray crystallography.In one case the preparation of a cycloalkaindole was possible by the irradiation of the α-chloro amide of an indol-3-yl alkanoic acid.