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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 12
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Original Articles

Efficient Synthesis of Hexahydrocarbazoles

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Pages 1752-1758 | Received 29 Jan 2010, Published online: 29 Apr 2011
 

Abstract

Selective reduction of the nitro group in methyl 1-(2-nitrophenyl)-4-oxo-cyclohex-2-enecarboxylates with zinc-acetic acid forms hexahydrocarbazoles. The reaction is applicable to the corresponding pyridyl analogs to generate azahexahydrocarbazoles. This provides an efficient method for the generation of tricyclic framework.

ACKNOWLEDGMENTS

The authors acknowledge Dr. Francisco Talamas and Dr. Josh Taygerly for their valuable input and the analytical department for providing the spectroscopic and physical data.

Notes

a All are isolated yields and are not optimized. Synthesis of cyclohexenones 2a–e are described in the previous paper.[ Citation 4 ]

a All are isolated yields and are not optimized.

b Isolated as an HCl salt.

Current name and affiliation for Christa Parmer: Christa Tatyosian, Bio-Rad Laboratories, Hercules, California, USA.

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