TY - JOUR
T1 - Synthesis of 3,4-bridged indoles by photocyclisation reactions. Part 1. Photocyclisation of halogenoacetyl tryptophan derivatives
AU - Beck, Anthony L.
AU - Mascal, Mark
AU - Moody, Christopher J.
AU - Slawin, Alexandra M Z
AU - Williams, David J.
AU - Coates, William J.
PY - 1992
Y1 - 1992
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=37049088832&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=37049088832&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:37049088832
SP - 797
EP - 812
JO - Journal of the Chemical Society. Perkin Transactions 1
JF - Journal of the Chemical Society. Perkin Transactions 1
SN - 1470-4358
IS - 7
ER -