In:
European Journal of Organic Chemistry, Wiley, Vol. 2004, No. 11 ( 2004-06), p. 2411-2420
Abstract:
A series of 1,1‐bis(indol‐3‐yl) and 1‐(indol‐2‐yl)‐1‐(indol‐3‐yl)‐ψ‐hydroxyalkanes, prepared from the corresponding indole derivatives and suitable hydroxyaldehydes via routine coupling reactions, were treated with DAST (diethylaminosulfur trifluoride) under mild conditions, to generate a small library of cycloalkanoindoles. Irrespective of the substitution pattern, i.e. whether they are symmetrical or unsymmetrical derivatives, the same mixture of products is produced, in which the tetrahydro‐1 H ‐carbazole and hexahydrocyclohepta[ b ]indole scaffolds are substituted by a indol‐3‐yl nucleus on one of the two α‐carbon atoms of the cycloalkane moieties. Thus, speculations on the reaction mechanism with the prediction of a common reaction intermediate are presented. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2004:11
DOI:
10.1002/ejoc.200300738
Language:
English
Publisher:
Wiley
Publication Date:
2004
detail.hit.zdb_id:
1475010-7
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