Issue 7, 1992

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

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1992, 797-811

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

A. L. Beck, M. Mascal, C. J. Moody, A. M. Z. Slawin, D. J. Williams and W. J. Coates, J. Chem. Soc., Perkin Trans. 1, 1992, 797 DOI: 10.1039/P19920000797

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