Palladium-Catalyzed anti-Michael-Type Hydroamination of N-(Quinolin-8-yl)acrylamide with 2-Pyridones

被引：1

作者：

Suzuki, Hirotsugu ^{[1
]}

Yamanokuchi, Soma ^{[2
]}

Moro, Ryota ^{[2
]}

Matsuda, Takanori ^{[2
]}

机构：

[1] Univ Fukui, Tenure Track Program Innovat Res, Fukui, Fukui 9108507, Japan

[2] Tokyo Univ Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 30期

关键词：

ALKYLATION; INHIBITORS; PYRIDONES; REGIO;

D O I：

10.1021/acs.orglett.4c02234

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here we report a palladium-catalyzed anti-Michael-type hydroamination of N-(quinolin-8-yl)acrylamide with 2-pyridones. The use of a palladium catalyst enables the alpha-addition of 2-pyridones, resulting in the formation of a range of N-substituted 2-pyridone carboxamides with yields ranging from 10% to 80%. Derivatization of the products highlights the utility of this transformation. Preliminary mechanistic investigations suggest that the reaction proceeds through the direct addition of a nitrogen atom of 2-pyridones, ruling out other pathways such as O-to-N-alkyl migration.

引用

页码：6444 / 6448

页数：5

共 27 条

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[3] Alkyl(quinolin-8-yl)phosphine Oxides as Hemilabile Preligands for Palladium-Catalyzed Reactions
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[6] Palladium-catalyzed rearrangement/arylation of 2-allyloxypyridine leading to the synthesis of N-substituted 2-pyridones
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[7] Cobalt-catalyzed electrochemical C-H/N-H functionalization of N-(quinolin-8-yl)benzamide with isocyanides
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[8] Cobalt(II)-Catalyzed C-H/N-H Functionalization and Annulation of N-(quinolin-8-yl)benzamide with Cyclopropanols
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[9] Tris{2-[N-(quinolin-8-yl)carbamoylmethoxy]phenyl}phosphine oxide: synthesis and coordination properties
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[10] The crystal structures of the ligand N-(quinolin-8-yl) pyrazine-2-carboxamide and of a tetranuclear copper(II) complex
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