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Synlett 2011(4): 587-588  
DOI: 10.1055/s-0030-1259533
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Iron-Acetic Acid: A Versatile Reductive Cyclizing Agent

Chintakunta Ramesh*
Department of Chemistry, National Taiwan Normal University, 88, Section 4, Tingchow Road, Taipei 116, Taiwan, ROC
e-Mail: rameshch_10@yahoo.co.in;
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Publication History

Publication Date:
08 February 2011 (online)

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Introduction

The iron-acetic acid system is an efficient agent for the reduction of aromatic nitro compounds into its corresponding amines. This transformation proceeds via the hydroxylamine, followed by azoxy and azo compounds to its corresponding aryl amines (Scheme  [¹] ). [¹] This system was discovered by Bechamp over 100 years ago. [²] However, the first published systematic study of the reduction of nitro compounds by iron-acetic acid appeared in 1977. [³]

Scheme 1

In recent years, iron-acetic acid is widely used for the ­reduction of nitro groups and subsequent cyclization in a variety of chemical transformations to synthesize biologically important structural units present in heterocyclic molecules. Iron powder is commercial available, of low cost, non-toxic, and environmentally friendly. In addition to this, its functional group tolerance, avoiding of side products, short reaction times, and a simple workup procedure makes iron-acetic acid a versatile reagent.