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Molecules 2017, 22(8), 1278; doi:10.3390/molecules22081278

An Efficient One-Pot Catalyzed Synthesis of 2,4-Disubstituted 5-Nitroimidazoles Displaying Antiparasitic and Antibacterial Activities

1
Aix Marseille University, Institut de Chimie Radicalaire ICR, UMR CNRS 7273, Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin—CS 30064, 13385 Marseille CEDEX 05, France
2
IHU Méditerranée Infection, Aix Marseille University, Unité de Recherche sur les Maladies Infectieuses et Tropicales Emergentes, URMITE UMR 63, CNRS 7278, IRD 198, Inserm 1095, Faculté de Médecine de la Timone, 19-21 Boulevard Jean Moulin, 13005 Marseille, France
3
Aix Marseille University, CNRS, IRD, Avignon Université, IMBE UMR 7263, Laboratoire de Mutagénèse Environnementale, 13385 Marseille, France
*
Author to whom correspondence should be addressed.
Received: 20 July 2017 / Accepted: 29 July 2017 / Published: 3 August 2017
(This article belongs to the Special Issue Multicomponent Reaction-Based Synthesis of Bioactive Molecules)
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Abstract

A one-pot regioselective bis-Suzuki-Miyaura or Suzuki-Miyaura/Sonogashira reaction on 2,4-dibromo-1-methyl-5-nitro-1H-imidazole under microwave heating was developed. This method is applicable to a wide range of (hetero)arylboronic acids and terminal alkynes. Additionally, this approach provides a simple and efficient way to synthesize 2,4-disubstituted 5-nitroimidazole derivatives with antibacterial and antiparasitic properties. View Full-Text
Keywords: 5-nitroimidazole; Suzuki-Miyaura/Sonogashira; regioselectivity; microwave; antiparasitic; antibacterial 5-nitroimidazole; Suzuki-Miyaura/Sonogashira; regioselectivity; microwave; antiparasitic; antibacterial
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Mathias, F.; Kabri, Y.; Okdah, L.; Di Giorgio, C.; Rolain, J.-M.; Spitz, C.; Crozet, M.D.; Vanelle, P. An Efficient One-Pot Catalyzed Synthesis of 2,4-Disubstituted 5-Nitroimidazoles Displaying Antiparasitic and Antibacterial Activities. Molecules 2017, 22, 1278.

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