Beilstein Arch. 2024, 202464. https://doi.org/10.3762/bxiv.2024.64.v1
Published 04 Nov 2024
The C–H arylation of 2-quinolinecarboxyamide bearing C–Br bond at the N-aryl moiety is carried out with a palladium catalyst. The reaction proceeds at the C–H bond on the pyridine ring adjacent to the amide group in the presence of 10 mol% Pd(OAc)2 at 110 °C to afford the cyclized product in 42% yield. The yield is improved to 94% when the reaction is performed with PPh3 as a ligand of palladium. The reaction is examined with amides derived from unsubstituted picoline, 6-methyl-picoline, and 2,6-pyridinedicarboxylic acid in a similar manner to afford the cyclized product in 70%, 77%, 87%, respectively. The related reaction is also carried out with amides of non-pyridine derivatives terephthal- and benz- amides to afford multiply-fused heterocyclic compounds in 81% and 89% yields, respectively.
Keywords: Intramolecular C–H arylation; palladium acetate; phosphine ligand; pyridine amides; multiply-fused heterocycles
| Format: PDF | Size: 2.3 MB | Download |
When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:
Nakanishi, Y.; Sugita, S.; Okano, K.; Mori, A. Beilstein Arch. 2024, 202464. doi:10.3762/bxiv.2024.64.v1
Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and
Zotero.
© 2024 Nakanishi et al.; licensee Beilstein-Institut.
This is an open access work licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-archives.org/xiv/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this work could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
