Intramolecular C-H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds.

IF 2.2 4区 化学 Q2 CHEMISTRY, ORGANIC Beilstein Journal of Organic Chemistry Pub Date : 2024-12-13 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.269
Yuki Nakanishi, Shoichi Sugita, Kentaro Okano, Atsunori Mori
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Abstract

The C-H arylation of 2-quinolinecarboxyamide bearing a 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-methylpicoline, and 2,6-pyridinedicarboxylic acid in a similar manner to afford the cyclized products in 70%, 77%, and 87% yield, respectively. The related reaction is also carried out with amides of non-pyridine derivatives terephthal- and benzamides to afford multiply fused heterocyclic compounds in 81% and 89% yields, respectively.

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来源期刊
CiteScore
4.90
自引率
3.70%
发文量
167
审稿时长
1.4 months
期刊介绍: The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
期刊最新文献
Intramolecular C-H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds. Non-covalent organocatalyzed enantioselective cyclization reactions of α,β-unsaturated imines. Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina. Discovery of ianthelliformisamines D-G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D. Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling.
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