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Gold‐Catalyzed Annulation of Ynamides with Aminocarbonyls as a Route to 2‐Aminoquinolines Diversely Substituted at the 4th‐Position. / Shcherbakov, Nikolay V.; Kotikova, Polina F.; Chikunova, Elena I.; Dar'in, Dmitry V.; Kukushkin, Vadim Yu.; Dubovtsev, Alexey Yu.

в: Advanced Synthesis and Catalysis, Том 365, № 14, 2023, стр. 2428-2434.

Результаты исследований: Научные публикации в периодических изданияхстатьяРецензирование

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@article{add30611e9c24d2bb78c3eb1f755c092,
title = "Gold‐Catalyzed Annulation of Ynamides with Aminocarbonyls as a Route to 2‐Aminoquinolines Diversely Substituted at the 4th‐Position",
abstract = "Gold-catalyzed interplay between ynamides and aminocarbonyls comprises a route to 2-aminoquinolines. This modular annulation proceeds under relatively mild conditions (Ph3PAuCl/AgNTf2 5 mol %, DCE, 60–80 °C), and a number of functionalities were compatible (42 examples; 25–98% yields). In contrast to a group of other gold-catalyzed methods employing the ynamide/amine combinations for the assembly of 2-aminoquinolines, the developed approach utilizes a diversity of aminocarbonyl substrates and, in particular, allows a variation of the substituents in the 4th quinoline position. The synthetic potential of the obtained heterocyclic products was illustrated by post-modifications of the quinoline backbone and the peripheral substituents.",
keywords = "Alkynes, Gold catalysis, Homogeneous catalysis, Quinolines, Synthetic methods",
author = "Shcherbakov, {Nikolay V.} and Kotikova, {Polina F.} and Chikunova, {Elena I.} and Dar'in, {Dmitry V.} and Kukushkin, {Vadim Yu.} and Dubovtsev, {Alexey Yu.}",
year = "2023",
doi = "10.1002/adsc.202300484",
language = "English",
volume = "365",
pages = "2428--2434",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-Blackwell",
number = "14",

}

RIS

TY - JOUR

T1 - Gold‐Catalyzed Annulation of Ynamides with Aminocarbonyls as a Route to 2‐Aminoquinolines Diversely Substituted at the 4th‐Position

AU - Shcherbakov, Nikolay V.

AU - Kotikova, Polina F.

AU - Chikunova, Elena I.

AU - Dar'in, Dmitry V.

AU - Kukushkin, Vadim Yu.

AU - Dubovtsev, Alexey Yu.

PY - 2023

Y1 - 2023

N2 - Gold-catalyzed interplay between ynamides and aminocarbonyls comprises a route to 2-aminoquinolines. This modular annulation proceeds under relatively mild conditions (Ph3PAuCl/AgNTf2 5 mol %, DCE, 60–80 °C), and a number of functionalities were compatible (42 examples; 25–98% yields). In contrast to a group of other gold-catalyzed methods employing the ynamide/amine combinations for the assembly of 2-aminoquinolines, the developed approach utilizes a diversity of aminocarbonyl substrates and, in particular, allows a variation of the substituents in the 4th quinoline position. The synthetic potential of the obtained heterocyclic products was illustrated by post-modifications of the quinoline backbone and the peripheral substituents.

AB - Gold-catalyzed interplay between ynamides and aminocarbonyls comprises a route to 2-aminoquinolines. This modular annulation proceeds under relatively mild conditions (Ph3PAuCl/AgNTf2 5 mol %, DCE, 60–80 °C), and a number of functionalities were compatible (42 examples; 25–98% yields). In contrast to a group of other gold-catalyzed methods employing the ynamide/amine combinations for the assembly of 2-aminoquinolines, the developed approach utilizes a diversity of aminocarbonyl substrates and, in particular, allows a variation of the substituents in the 4th quinoline position. The synthetic potential of the obtained heterocyclic products was illustrated by post-modifications of the quinoline backbone and the peripheral substituents.

KW - Alkynes

KW - Gold catalysis

KW - Homogeneous catalysis

KW - Quinolines

KW - Synthetic methods

UR - https://www.mendeley.com/catalogue/bb75f218-f023-3cd7-a8ad-cd5b65900e81/

U2 - 10.1002/adsc.202300484

DO - 10.1002/adsc.202300484

M3 - Article

VL - 365

SP - 2428

EP - 2434

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 14

ER -

ID: 110778153