Unusual rearrangement of imidazo[1,5- a]imidazoles and imidazo[1,2- b]pyrazoles into imidazo[1,5- a]pyrimidines and pyrazolo[1,5- a]pyrimidines

Khadija Gambouz; Mohsine Driowya; Mohammed Loubidi; Zahira Tber; Hassan Allouchi; Saïd El Kazzouli; Mohamed Akssira; Gérald Guillaumet

doi:10.1039/c9ra04609g

Unusual rearrangement of imidazo[1,5- a]imidazoles and imidazo[1,2- b]pyrazoles into imidazo[1,5- a]pyrimidines and pyrazolo[1,5- a]pyrimidines

RSC Adv. 2019 Sep 16;9(50):29051-29055. doi: 10.1039/c9ra04609g. eCollection 2019 Sep 13.

Authors

Khadija Gambouz^{1

2

3}, Mohsine Driowya³, Mohammed Loubidi^{1

3}, Zahira Tber^{1

3}, Hassan Allouchi⁴, Saïd El Kazzouli², Mohamed Akssira¹, Gérald Guillaumet³

Affiliations

¹ Laboratoire de Chimie Physique et Chimie Bioorganique, URAC 22 FSTM, Université Hassan II - Casablanca Morocco mohamed.akssira@fstm.ac.ma.
² Euromed Research Center, Euromed Faculty of Enginnering, Euromed University of Fes (UEMF) Route de Meknès 30000 Fès Morocco s.elkazzouli@ueuromed.org.
³ Institut de Chimie Organique et Analytique, Université d'Orléans, UMR CNRS 7311 45067 Orléans Cedex 2 BP 6759 France gerald.guillaumet@univ-orleans.fr.
⁴ Laboratoire de Chimie Physique, équipe EA 7502 SIMBA, Faculté de Pharmacie, Université de Tours 31, avenue Monge 37200 Tours France.

Abstract

A multicomponent reaction giving easy and cheap access to a variety of bicyclic 5,5-fused hetero-rings has been developed. Then, an usual rearrangement of imidazo[1,5-a]imidazoles or imidazo[1,2-b]pyrazoles leading to bi-heterocyclic imidazo- and pyrazolo[1,5-a]pyrimidines in the presence of a specific amount of I₂ in THF at room temperature has been achieved. This new method enables the hitherto unreported synthesis of functionalized imidazo- and pyrazolo[1,5-a]pyrimidines.