Synthesis of 3,4-bridged indoles by photocyclisation reactions. Part 1. Photocyclisation of halogenoacetyl tryptophan derivatives

Anthony L. Beck, Mark Mascal, Christopher J. Moody, Alexandra M Z Slawin, David J. Williams, William J. Coates

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

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[c,d]indole was possible by the irradiation of the α-chloro amide of an indol-3-yl alkanoic acid.

Original languageEnglish (US)
Pages (from-to)797-812
Number of pages16
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number7
StatePublished - 1992
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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