Synthesis 2019; 51(21): 3973-3980
DOI: 10.1055/s-0039-1690182
paper
© Georg Thieme Verlag Stuttgart · New York

One-Step Synthesis of 1H-Imidazo[1,5-a]imidazole Scaffolds and Access to their Polyheterocycles

a  Institut de Chimie Organique et Analytique, Université d’Orléans, UMR CNRS 7311, BP 6759, 45067 Orléans Cedex, France   Email: gerald.guillaumet@univ-orleans.fr
b  Laboratoire de Chimie Physique & de Chimie Bioorganique, URAC 22 Université Hassan II Casablanca, BP 146, 28800 Mohammedia, Morocco   Email: akssira.m@gmail.com
,
M. Lorion
c  Greenpharma S.A.S., 3, allée du Titane, 45100 Orléans, France
,
A. El Hakmaoui
b  Laboratoire de Chimie Physique & de Chimie Bioorganique, URAC 22 Université Hassan II Casablanca, BP 146, 28800 Mohammedia, Morocco   Email: akssira.m@gmail.com
,
P. Bernard
c  Greenpharma S.A.S., 3, allée du Titane, 45100 Orléans, France
,
M. Akssira
b  Laboratoire de Chimie Physique & de Chimie Bioorganique, URAC 22 Université Hassan II Casablanca, BP 146, 28800 Mohammedia, Morocco   Email: akssira.m@gmail.com
,
G. Guillaumet
a  Institut de Chimie Organique et Analytique, Université d’Orléans, UMR CNRS 7311, BP 6759, 45067 Orléans Cedex, France   Email: gerald.guillaumet@univ-orleans.fr
› Author Affiliations
Further Information

Publication History

Received: 12 March 2019

Accepted after revision: 27 July 2019

Publication Date:
21 August 2019 (eFirst)

Abstract

In this work, we continue our adventure in the chemistry of 5-5 tri-nitrogen bicycles. We disclose herein a one-step reaction to synthesize 1H-imidazo[1,5-a]imidazoles with different substituents introduced through the use of a wide range of aldehydes and isocyanides by using a Groebke–Blackburn–Bienaymé multicomponent reaction. The aim is to build a new library of 1H-imidazo[1,5-a]imidazole scaffolds. This bicycle was then modified to access new nitrogen-containing polycyclic compounds.

Supporting Information

 
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