New synthesis of imidazole derivatives from cyanobenzenes

Maxime Beuvin (1) , Maxime Manneveau (1) , Sonia Diab (1) , Baptiste Picard (1) , Serge Piettre (1) , M. Sanselme (2) , Julien Legros (1) , Isabelle Chataigner (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 SMS - Sciences et Méthodes Séparatives

An efficient access to 4-aryl imidazole scaffolds is described in two steps and one operation. Cyanoaryl-imidazolines are easily obtained by a (3 + 2) heterocyloaddition involving cyanobenzenes as dipolarophiles and a non-stabilized azomethine ylide as an electron-rich 1,3-dipole. Oxidation of the crude mixture affords an efficient two-steps access to the corresponding imidazoles.

Domains: Chemical Sciences

Maxime Beuvin, Maxime Manneveau, Sonia Diab, Baptiste Picard, Serge Piettre, et al.. New synthesis of imidazole derivatives from cyanobenzenes. Tetrahedron Letters, 2018, 59 (51), pp.4487-4491. ⟨10.1016/j.tetlet.2018.11.020⟩. ⟨hal-02024472⟩