Development of Novel and Efficient Processes for the Synthesis of 5-Amino and 5-Iminoimidazo[1,2- a]imidazoles via Three-Component Reaction Catalyzed by Zirconium(IV) Chloride

Mohsine Driowya; Régis Guillot; Pascal Bonnet; Gérald Guillaumet

doi:10.3389/fchem.2019.00457

Development of Novel and Efficient Processes for the Synthesis of 5-Amino and 5-Iminoimidazo[1,2- a]imidazoles via Three-Component Reaction Catalyzed by Zirconium(IV) Chloride

Front Chem. 2019 Jul 8:7:457. doi: 10.3389/fchem.2019.00457. eCollection 2019.

Authors

Mohsine Driowya¹, Régis Guillot², Pascal Bonnet¹, Gérald Guillaumet¹

Affiliations

¹ Institut de Chimie Organique et Analytique, Université d'Orléans, UMR CNRS 7311, Orléans, France.
² Institut de Chimie Moléculaire et des Matériaux d'Orsay, Université Paris Sud, Université Paris Saclay, UMR CNRS 8182, Orsay, France.

Abstract

General and efficient approaches for the synthesis of new 5-amino and 5-iminoimidazo[1,2-a]imidazoles were developed through a three-component reaction of 1-unsubstituted 2-aminoimidazoles with various aldehydes and isocyanides mediated by zirconium(IV) chloride. The protocols were established considering the reactivity of the starting substrate, which varies depending on the presence of a substituent on the 2-aminoimidazole moiety. A library of new N-fused ring systems with wide structural diversification, novel synthetic, and potential pharmacological interest was obtained in moderate to good yields.

Keywords: 2-aminoimidazole; N-heterocycles; catalysis; fused-ring systems; isocyanide Ugi reaction; multicomponent reactions; zirconium(IV) chloride.