TY - JOUR
T1 - A Facile One-Pot Synthesis of New Poly Functionalized Pyrrolotriazoles via a Regioselective Multicomponent Cyclisation and Suzuki–Miyaura Coupling Reactions
AU - Garnier, Simon
AU - Brugemann, Kévin
AU - Zak, Agnieszka
AU - Vercouillie, Johnny
AU - Potier-Cartereau, Marie
AU - Marchivie, Mathieu
AU - Routier, Sylvain
AU - Buron, Frédéric
N1 - Funding Information:
Authors gratefully acknowledge major financial support from the Ligue contre le Cancer du Grand Ouest (comités des Deux Sèvres, du Finistère, de l’Ile et Villaine, du Loir et Cher, de Loire Atlantique, du Loiret, de la Vienne), the Canceropôle Grand Ouest, INCA, Région Centre Val de Loire, the SFR neuroimagerie (SFR FED 4224), which made this study possible, and also the projects CHemBio (FEDER-FSE 2014-2020-EX003677), Techsab (FEDER-FSE 2014-2020-EX011313), the RTR Motivhealth (2019-00131403) and the Labex programs SYNORG (ANR-11-LABX-0029) and IRON (ANR-11-LABX-0018-01) for their financial support of ICOA, UMR 7311, University of Orléans, CNRS. We thank the Salsa platform of ICOA for facilities in analytical chemistry.
Publisher Copyright:
© 2022 by the authors.
PY - 2022/8
Y1 - 2022/8
N2 - 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.
AB - 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.
KW - Suzuki–Miyaura reaction
KW - multicomponent cyclisation
KW - pyrrolo[2,3-d][1,2,3]triazoles
UR - http://www.scopus.com/inward/record.url?scp=85137370528&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85137370528&partnerID=8YFLogxK
U2 - 10.3390/catal12080828
DO - 10.3390/catal12080828
M3 - Article
AN - SCOPUS:85137370528
SN - 2073-4344
VL - 12
JO - Catalysts
JF - Catalysts
IS - 8
M1 - 828
ER -