Elsevier

Tetrahedron Letters

Volume 50, Issue 31, 5 August 2009, Pages 4423-4426
Tetrahedron Letters

Straightforward selective preparation of nitro- or amino-indoles from 2-halonitroanilines and alkynes. First synthesis of 7-amino-5-nitroindoles

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Abstract

A one-pot selective synthesis of 2-substituted C5-, C6-, and C7-nitro- or amino-indoles has been developed from 2-halonitroanilines. These two types of nitrogen-substituted indoles have been selectively obtained by only varying the solvent used in the tandem Sonogashira coupling/heteroannulation reaction. Moreover, from commercially available 2-bromo-4,6-dinitroaniline an unprecedented in situ selective reduction of one of the nitro groups has allowed the synthesis of new 7-amino-5-nitro-2-substituted indoles.

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Acknowledgments

We gratefully thank Ministerio de Educación y Ciencia (MEC) and FEDER (CTQ2007-61436/BQU) and Junta de Castilla y León (BU021A09) for financial support. V.G. thanks MEC for a FPU predoctoral fellowship. Many thanks are due to Dr. F. Rodríguez (Universidad de Oviedo) for helpful comments.

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