Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones

Xiaochen Du; Jianjun Huang; Anton A. Nechaev; Ruwei Yao; Jing Gong; Erik V. Van Der Eycken; Olga P. Pereshivko; Vsevolod A. Peshkov

doi:10.3762/bjoc.14.234

Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones

Xiaochen Du, Jianjun Huang, Anton A. Nechaev, Ruwei Yao, Jing Gong, Erik V. Van Der Eycken, Olga P. Pereshivko, Vsevolod A. Peshkov

Research output: Contribution to journal › Article

6 Citations (Scopus)

Abstract

A series of propargylamides containing an electron-rich benzene ring was prepared through the Ugi reaction of 3,5-dimethoxy-aniline with various propiolic acids, aldehydes and isocyanides. Subjecting these adducts to a gold-catalyzed intramolecular alkyne hydroarylation process allowed to efficiently construct the 2-quinolone core bearing a branched substituent on the nitrogen atom.

Original language	English
Pages (from-to)	2572-2579
Number of pages	8
Journal	Beilstein Journal of Organic Chemistry
Volume	14
DOIs	https://doi.org/10.3762/bjoc.14.234
Publication status	Published - Oct 4 2018

Keywords

2-quinolones
Gold catalysis
Hydroarylation
Ugi reaction

ASJC Scopus subject areas

Organic Chemistry

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10.3762/bjoc.14.234

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Du, X., Huang, J., Nechaev, A. A., Yao, R., Gong, J., Van Der Eycken, E. V., Pereshivko, O. P., & Peshkov, V. A. (2018). Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones. Beilstein Journal of Organic Chemistry, 14, 2572-2579. https://doi.org/10.3762/bjoc.14.234

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abstract = "A series of propargylamides containing an electron-rich benzene ring was prepared through the Ugi reaction of 3,5-dimethoxy-aniline with various propiolic acids, aldehydes and isocyanides. Subjecting these adducts to a gold-catalyzed intramolecular alkyne hydroarylation process allowed to efficiently construct the 2-quinolone core bearing a branched substituent on the nitrogen atom.",

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doi = "10.3762/bjoc.14.234",

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AU - Du, Xiaochen

AU - Huang, Jianjun

AU - Nechaev, Anton A.

AU - Yao, Ruwei

AU - Gong, Jing

AU - Van Der Eycken, Erik V.

AU - Pereshivko, Olga P.

AU - Peshkov, Vsevolod A.

PY - 2018/10/4

Y1 - 2018/10/4

N2 - A series of propargylamides containing an electron-rich benzene ring was prepared through the Ugi reaction of 3,5-dimethoxy-aniline with various propiolic acids, aldehydes and isocyanides. Subjecting these adducts to a gold-catalyzed intramolecular alkyne hydroarylation process allowed to efficiently construct the 2-quinolone core bearing a branched substituent on the nitrogen atom.

AB - A series of propargylamides containing an electron-rich benzene ring was prepared through the Ugi reaction of 3,5-dimethoxy-aniline with various propiolic acids, aldehydes and isocyanides. Subjecting these adducts to a gold-catalyzed intramolecular alkyne hydroarylation process allowed to efficiently construct the 2-quinolone core bearing a branched substituent on the nitrogen atom.

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KW - Gold catalysis

KW - Hydroarylation

KW - Ugi reaction

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