Tetrahedron Letters

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

R Sanz, V Guilarte, A Pérez

Index: Sanz, Roberto; Guilarte, Veronica; Perez, Antonio Tetrahedron Letters, 2009 , vol. 50, # 31 p. 4423 - 4426

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Citation Number: 19

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 ...