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

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  1 , Régis Guillot  2 , Pascal Bonnet  1 , Gérald Guillaumet  1
Affiliations

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 et al. Front Chem. .

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.

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Figure 1
Figure 1
ORTEP representation of compound 4a.
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