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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2008 - Issue 1
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Original Articles

Efficient and Straightforward Synthesis of Tetrahydrocarbazoles and 2,3-Dimethyl Indoles Catalyzed by CAN

, , &
Pages 158-165 | Received 04 Apr 2008, Published online: 15 Feb 2011
 

Abstract

A simple protocol was established to synthesize 2,3-dialkyl indoles and various tetrahydrocarbazoles via Fischer indole synthesis. This method uses ceric ammonium nitrate as a catalyst for the Fischer indole synthesis with substituted phenyl hydrazine hydrochlorides and 2-butanone, phenyl propanal, and cyclohexanone. This process is a practical synthetic method for the preparation of various 2,3-disubstituted alkyl indoles and tetrahydrocarbazoles.

ACKNOWLEDGMENTS

We are thankful to the Department of Postgraduate Studies and Research in Industrial Chemistry and Chemistry, Kuvempu University, Shankaraghatta, for providing laboratory facilities. The authors are also thankful to the Indian Institute of Science, Bangalore, for spectral data.

Notes

Note. All reactions were carried out at reflux temperature.

a isolated yields.

a All reactions were carried out at reflux temperature.

b Isolated yields.

a All reactions were carried out at reflux temperature.

b Isolated yields.

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