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Cobalt- and Iron-Catalyzed Redox Condensation of o-Substituted Nitrobenzenes with Alkylamines: A Step- and Redox-Economical Synthesis of Diazaheterocycles

Thanh Binh Nguyen*, Julie Le Bescont, Ludmila Ermolenko and Ali Al-Mourabit

*Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France, Email: nguyenicsn.cnrs-gif.fr

T. B. Nguyen, J. Le Bescont, L. Ermolenko, A. Al-Mourabit, Org. Lett., 2013, 15, 6218-6221.

DOI: 10.1021/ol403064z (free Supporting Information)


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Abstract

A broad range of functionalized 2-aryl benzimidazoles can be prepared by a solvent-free cobalt- or iron-catalyzed redox condensation of 2-nitroanilines and benzylamines via benzylamine oxidation, nitro reduction, condensation, and aromatization without any reducing or oxidizing agent. The method can be extended to afford various other diazaheterocycles.

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Sodium Sulfide: A Sustainable Solution for Unbalanced Redox Condensation Reaction between o-Nitroanilines and Alcohols Catalyzed by an Iron-Sulfur System

T. B. Nguyen, L. Ermolenko, A. Al-Mourabit, Synthesis, 2015, 47, 1741-1748.

Benzazoles from Aliphatic Amines and o-Amino/Mercaptan/Hydroxyanilines: Elemental Sulfur as a Highly Efficient and Traceless Oxidizing Agent

T. B. Nguyen, L. Ermolenko, W. A. Dean, A. Al-Mourabit, Org. Lett., 2012, 14, 5948-5951.


Key Words

benzimidazoles


ID: J54-Y2013