On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters

Anthony Martin (1) , Diana Cheshmedzhieva (2) , Valeria Palermo (1, 3) , Frédéric Liéby-Muller (1, 4) , Gustavo P Romanelli (3) , Anouk Gaudel-Siri (5) , Yoann Coquerel (1) , Thierry Constantieux (1) , Jean Rodriguez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 Sofia University "St. Kliment Ohridski"
3 UNLP - Universidad Nacional de la Plata [Argentine]
4 Centre de R&D Pierre Fabre - Centre de Recherche Pierre Fabre
5 ICR - Institut de Chimie Radicalaire

The regioselectivity of molecular sieves-promoted oxidative three-component reaction between -ketoesters, aromatic o-diamines and acrolein, leading to pyrido[1,2-a]benzimidazoles, has been investigated by a combination of experimental and theoretical studies. Molecular sieves act both as heterogeneous catalyst and dehydrating agent and their role has been modeled in the theoretical approach. The modulation of the reactivity of the aromatic diamine partner as a function of the nature of the substituents of the aromatic ring and its influence on the regioselectivity of the reaction could be rationalized.

Mots clés: Multicomponent reaction; Michael addition; Benzimidazole; Molecular sieves; Heterocycles

Domaines: Chimie organique

Anthony Martin, Diana Cheshmedzhieva, Valeria Palermo, Frédéric Liéby-Muller, Gustavo P Romanelli, et al.. On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters. Comptes Rendus. Chimie, 2022, 25 (G1), pp.19-29. ⟨10.5802/crchim.137⟩. ⟨hal-03777692⟩