A Facile One-Pot Synthesis of New Poly Functionalized Pyrrolotriazoles via a Regioselective Multicomponent Cyclisation and Suzuki–Miyaura Coupling Reactions
Simon Garnier,
Kévin Brugemann,
Agnieszka Zak,
Johnny Vercouillie,
Marie Potier-Cartereau,
Mathieu Marchivie,
Sylvain Routier,
Frédéric Buron
Affiliations
Simon Garnier
Institut de Chimie Organique et Analytique, ICOA, Université d’Orleans, CNRS UMR 7311, Rue de Chartres, BP 6759, 45067 Orléans, France
Kévin Brugemann
Institut de Chimie Organique et Analytique, ICOA, Université d’Orleans, CNRS UMR 7311, Rue de Chartres, BP 6759, 45067 Orléans, France
Agnieszka Zak
Institut de Chimie Organique et Analytique, ICOA, Université d’Orleans, CNRS UMR 7311, Rue de Chartres, BP 6759, 45067 Orléans, France
Johnny Vercouillie
iBrain, INSERM, UMR 1253, Université de Tours, 37032 Tours, France
Marie Potier-Cartereau
Nutrition, Croissance et Cancer, N2C, INSERM, UMR 1069, Université de Tours, 37032 Tours, France
Mathieu Marchivie
CNRS, Bordeaux INP, ICMCB, UMR 5026, University Bordeaux, 33600 Pessac, France
Sylvain Routier
Institut de Chimie Organique et Analytique, ICOA, Université d’Orleans, CNRS UMR 7311, Rue de Chartres, BP 6759, 45067 Orléans, France
Frédéric Buron
Institut de Chimie Organique et Analytique, ICOA, Université d’Orleans, CNRS UMR 7311, Rue de Chartres, BP 6759, 45067 Orléans, France
The first access to N-1, N-4 disubstituted pyrrolo[2,3-d][1,2,3]triazoles is reported. The series were generated using a “one-pot” MCR, leading to a single regioisomer of the attempted heteroaromatic skeleton in good yields. Next, the functionalization of C-5 and C-6 positions was investigated. (Het)aryl groups were introduced at the C-5 and C-6 positions of the pyrrolo[2,3-d][1,2,3]triazoles using regioselective electrophilic brominations followed by Suzuki–Miyaura cross coupling reactions. Palladium-catalyzed cross-coupling conditions were optimized and a representative library of various boronic acids was employed to establish the scope and limitations of the method.