Journal of the Chemical Society. Perkin transactions I p. 797 - 812 (1992)
Update date:2022-08-02
Topics:
Beck, Anthony L.
Mascal, Mark
Moody, Christopher J.
Slawin, Alexandra M. Z.
Williams, David J.
Coates, William J.
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 cycloalka
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