Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Methanal Extrusion in ipso-Substitution Reactions of Hydroxymethylindoles*

Jeremy C. Dobrowolski A , Kittiya Somphol A , Mardi Santoso A , Hung Duong A , Christopher R. Gardner A , Naresh Kumar A and David StC. Black A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry, The University of New South Wales, UNSW Australia, Sydney, NSW 2052, Australia.

B Corresponding author. Email: d.black@unsw.edu.au

Australian Journal of Chemistry 70(11) 1188-1195 https://doi.org/10.1071/CH17257
Submitted: 12 May 2017  Accepted: 2 August 2017   Published: 29 August 2017

Abstract

A range of 3-hydroxymethylindoles undergo acid-catalysed reactions involving ipso-electrophilic substitution with the extrusion of methanal and the formation of diindolylmethane moieties. Both inter- and intramolecular processes lead to macrocyclic compounds 10 and 14.


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