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

Thanh Binh Nguyen*, Ludmila Ermolenko, William A. Dean 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, L. Ermolenko, W. A. Dean, A. Al-Mourabit, Org. Lett., 2012, 14, 5948-5951.

DOI: 10.1021/ol302856w

see article for more reactions

Abstract

The use of elemental sulfur as traceless oxidizing agent enables a remarkably simple solvent-free and catalyst-free synthesis of benzazoles from alkylamines and o-hydroxy/amino/mercaptan anilines.

see article for more examples

Elemental Sulfur-Promoted Oxidative Rearranging Coupling between o-Aminophenols and Ketones: A Synthesis of 2-Alkyl benzoxazoles under Mild Conditions

T. B. Nguyen, P. Retailleau, Org. Lett., 2017, 19, 3887-3890.

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

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

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.

Key Words

benzimidazoles, benzothiazoles

ID: J54-Y2012-3740