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Journal articles
A Straightforward One-Step Access to Ticlopidine Derivatives Arylated at the C5-Position of the Thienyl Ring via Pd-Catalyzed Direct Arylations
Abstract : The reactivity of Ticlopidine, which belongs to the thienopyridine drug family, in Pd-catalyzed C-H bond functionalization was investigated. The use of a palladium-diphosphine catalyst associated to potassium acetate base in N,N-dimethylacetamide was found to promote the regioselective arylation at the C5-position of the Ticlopidine thienyl ring with aryl bromides in high yields. In the course of this reaction, no dechlorination or debenzylation of the 2-chlorobenzyl group of Ticlopidine was observed. A wide variety of substituents on the aryl bromide was tolerated, such as nitro, nitrile, acetyl, propionyl, benzoyl, ester, chloro, fluoro or trifluoromethyl. Bromopyridines and bromoquinolines were also successfully employed. This methodology gives a one-step access to arylated Ticlopidine derivatives from commercially available compounds via a straightforward C-H bond functionalization procedure. Therefore, it provides a very appealing method to build a library of compounds containing a Ticlopidine unit.
Cited literature [37 references]
https://hal-univ-rennes1.archives-ouvertes.fr/hal-02391908
Contributor : Laurent Jonchère Connect in order to contact the contributor
Submitted on : Monday, December 9, 2019 - 2:53:23 PM
Last modification on : Wednesday, April 7, 2021 - 3:18:12 PM
Long-term archiving on: : Tuesday, March 10, 2020 - 9:00:13 PM
Contributor : Laurent Jonchère Connect in order to contact the contributor
Submitted on : Monday, December 9, 2019 - 2:53:23 PM
Last modification on : Wednesday, April 7, 2021 - 3:18:12 PM
Long-term archiving on: : Tuesday, March 10, 2020 - 9:00:13 PM
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