Synthesis of Imine and Amine-Linked Macrocycles Containing Tris-Indoles*
Hakan Kandemir A B , Ibrahim F. Sengul A C , Naresh Kumar A and David StC. Black A D
+ Author Affiliations
- Author Affiliations
A School of Chemistry, University of New South Wales (UNSW), Sydney, NSW 2052, Australia.
B Department of Chemistry, Faculty of Art and Science, Namık Kemal University, Tekirdag 59100, Turkey.
C Department of Chemistry, Gebze Technical University, PO Box 141, Kocaeli 41400, Turkey.
D Corresponding author. Email: d.black@unsw.edu.au
Australian Journal of Chemistry 70(11) 1196-1201 https://doi.org/10.1071/CH17264
Submitted: 15 May 2017 Accepted: 9 August 2017 Published: 1 September 2017
Abstract
The synthesis of 21-membered imine- and amine-linked tris-indole macrocycles starting from 7-nitroethylindoles is described. The 7-nitroethylindoles are converted to 2,2′-diindolylmethanes and the nitro groups reduced to amino. The resulting diamines undergo reactions with indole-2,7-dicarbaldehydes to form the macrocyclic imines, which can subsequently be reduced to the macrocyclic amines.
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