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Acid-Catalyzed Reactions of 3-Substituted-4,6-dimethoxyindoles with Ketones

Kasey Wood ^A , David StC. Black ^A ^B and Naresh Kumar ^A ^B

+ Author Affiliations

- Author Affiliations

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

^B Corresponding authors. Email: d.black@unsw.edu.au; n.kumar@unsw.edu.au

Australian Journal of Chemistry 63(5) 761-770 https://doi.org/10.1071/CH10137
Submitted: 22 March 2010 Accepted: 21 April 2010 Published: 21 May 2010

Abstract

Activated 3-substituted-4,6-dimethoxyindoles undergo acid catalyzed condensation with acetone and acetophenones in the presence of hydrochloric acid to give pyrrolo[a]indoles. Mixed pyrrolo[a]indoles can similarly be formed using a 1:1 mixture of two indoles. The reaction was found to be sensitive to acidity, with a 3:2 spiro condensation product being preferentially formed in the presence of p-toluenesulfonic acid.

Acknowledgements

We thank the University of New South Wales and the Australian Research Council for financial support.

References

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[29] Crystallographic data for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 769613 (7d) and CCDC 770366 (8a). X-ray crystal structures were obtained by Donald Craig, Crystallography Laboratory, UNSW Analytical Centre, Sydney, Australia.