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

Fanny Mathias (1) , Youssef Kabri (2) , Liliane Okdah (3) , Carole Di Giorgio (4) , Jean-Marc Rolain (5) , Cédric Spitz (2) , Maxime D Crozet (2) , Patrice Vanelle (2)

1 AMU PHARM - Aix-Marseille Université - Faculté de pharmacie
2 ICR - Institut de Chimie Radicalaire
3 IHU Marseille - Institut Hospitalier Universitaire Méditerranée Infection
4 IMBE - Institut méditerranéen de biodiversité et d'écologie marine et continentale
5 URMITE - Unité de Recherche sur les Maladies Infectieuses et Tropicales Emergentes

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.

Mots clés: regioselectivity; microwave; Suzuki-Miyaura/Sonogashira; antibacterial; antiparasitic; 5-nitroimidazole

Domaines: Chimie thérapeutique; Chimie organique

Fanny Mathias, Youssef Kabri, Liliane Okdah, Carole Di Giorgio, Jean-Marc Rolain, et al.. An Efficient One-Pot Catalyzed Synthesis of 2,4-Disubstituted 5-Nitroimidazoles Displaying Antiparasitic and Antibacterial Activities. Molecules, 2017, 22 (8), pp.1278. ⟨10.3390/molecules22081278⟩. ⟨hal-02096360⟩