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

MARTIN, ANTHONY; CHESHMEDZHIEVA, DIANA; PALERMO, VALERIA; LIÉBY-MULLER, FRÉDÉRIC; ROMANELLI, GUSTAVO P.; GAUDEL-SIRI, ANOUK; COQUEREL, YOANN; CONSTANTIEUX, THIERRY; RODRIGUEZ, JEAN

Comptes Rendus. Chimie

Elsevier

Año: 2022 vol. 25 p. 19 - 29

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