6154-30-9Relevant articles and documents
Efficient Access to Original 6-Substituted 5-Nitro-2,3-dihydro-imidazo[2,1- b ]oxazoles
Mathias, Fanny,Kabri, Youssef,Crozet, Maxime D.,Vanelle, Patrice
, p. 2775 - 2785 (2017)
A one-pot sequential intramolecular cyclization and Suzuki-Miyaura or Sonogashira reaction under microwave irradiation are reported in the 5-nitro-2,3-dihydroimidazo[2,1- b ]oxazole series. The intramolecular cyclization of 1-(2,4-dibromo-5-nitro-1 H -imidazol-1-yl)propan-2-ol between the hydroxyethyl group and the bromine atom at the 2-position is carried out first, followed by optimization and generalization of the Suzuki-Miyaura and Sonogashira cross-coupling reactions of the bromine atom at the 4-position. The various boronic acids and alkynyl derivatives used to perform these palladium-catalyzed cross-coupling reactions allowed to substitute the 6-position of 5-nitro-2,3-dihydroimidazo[2,1- b ]oxazole compounds.
Bromination of 5(4)-Nitroimidazole-4(5)-carboxylic Acid
Bakulev, V. A.,Mokrushin, V. S.,Pushkareva, Z. V.
, p. 539 (1982)
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An efficient one-pot catalyzed synthesis of 2,4-disubstituted 5-nitroimidazoles displaying antiparasitic and antibacterial activities
Mathias, Fanny,Kabri, Youssef,Okdah, Liliane,Giorgio, Carole Di,Rolain, Jean-Marc,Spitz, Cédric,Crozet, Maxime D.,Vanelle, Patrice
, (2017/08/30)
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.