Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains

Layal Hariss (1) , Kamal Bou Hadir (2) , Mirvat El-Masri (1) , Thierry Roisnel (3) , René Grée (3) , Ali Hachem (1)

1 LU - Lebanese University [Beirut]
2 AUB - American University of Beirut [Beyrouth]
3 ISCR - Institut des Sciences Chimiques de Rennes

Using an aerobic oxidative coupling, different new imidazo[1,2-]--heterocycles with -difluroroalkyl side chains have been prepared in fair yields by the reaction of -difluoroenones with aminopyridines, -pyrimidines and -pyridazines. Condensed heterocycles of this type play an important role as key core structures of various bioactive compounds. Further, starting with a chloroimidazopyridazine derivative, Pd-catalyzed coupling reactions as well as nucleophilic substitutions have been performed successfully in order to increase the molecular diversity.

Keywords: propargylic fluorides; aerobic oxidative coupling; imidazo[1; gem-difluoroalkyl derivatives; 2-a]-N-heterocycles

Domains: Chemical Sciences; Organic chemistry

Layal Hariss, Kamal Bou Hadir, Mirvat El-Masri, Thierry Roisnel, René Grée, et al.. Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains. Beilstein Journal of Organic Chemistry, 2017, 13, pp.2115-2121. ⟨10.3762/bjoc.13.208⟩. ⟨hal-01631917⟩