A new synthetic approach to the imidazo[1,5-a]imidazole-2-one scaffold and effective functionalization through Suzuki–Miyaura cross coupling reactions

We report herein a synthetic pathway to new 7-bromo-1-(4-methoxybenzyl)-5-methyl-imidazo[1,5- a ]imidazole-2-one. The synthetic potential of this scaffold was demonstrated by displacing bromine by Suzuki–Miyaura cross-coupling reactions. A large panel of boronic acids (aryl, heteroaryl or vinyl) wer...

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Bibliographic Details
Published in:RSC advances 2016, Vol.6 (9), p.7229-7238
Main Authors: Loubidi, M., Pillard, C., El Hakmaoui, A., Bernard, P., Akssira, M., Guillaumet, G.
Format: Article
Language:English
Subjects:
Aromatic compounds
Bromine
Chemical reactions
Cross coupling
Displacement
Libraries
Pathways
Scaffolds
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Summary:We report herein a synthetic pathway to new 7-bromo-1-(4-methoxybenzyl)-5-methyl-imidazo[1,5- a ]imidazole-2-one. The synthetic potential of this scaffold was demonstrated by displacing bromine by Suzuki–Miyaura cross-coupling reactions. A large panel of boronic acids (aryl, heteroaryl or vinyl) were easily introduced, giving access to a broad and diversified library of 1-(4-methoxybenzyl)-5-methyl-7-(substituted)-imidazo[1,5- a ]imidazole-2-ones.
ISSN:2046-2069
2046-2069
DOI:10.1039/C5RA25520A