Organic Letters, volume 24, issue 9, pages 1859-1864

Copper-Catalyzed Divergent C–H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines

Guang Yang ¹

Zhicheng Xiong ¹

Hongsheng Nie ¹

Meiqin He ¹

Qiong Feng ¹

Xuan Li ¹

Huabin Huang ¹

Shoucai Wang ¹

Fanghua Ji ¹

Guangbin Jiang ¹

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Guangxi Key Laboratory of Electrochemical and Magnetochemical Function Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, People’s Republic of China |

Publication type: Journal Article

Publication date: 2022-02-28

American Chemical Society (ACS)

Journal: Organic Letters

Quartile SCImago

Quartile WOS

Impact factor: 5.2

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.2c00454

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Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

With control by N1-substituents, the switchable divergent C-H functionalization reaction of quinoxalin-2(1H)-ones is achieved for the synthesis of (Z)-enaminones and furo[2,3-b]quinoxalines using the combination of a copper catalyst and an oxidant. This new protocol features mild reaction conditions, readily available materials, and a broad substrate scope. Gram-scale and mechanistic studies were also investigated. Furthermore, the desired products exhibited excellent antitumor activity against A549, HepG-2, MCF-7, and HeLa cells, which were tested by MTT assay.

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Yang G. et al. Copper-Catalyzed Divergent C–H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines // Organic Letters. 2022. Vol. 24. No. 9. pp. 1859-1864.

GOST all authors (up to 50) Copy

Yang G., Xiong Z., Nie H., He M., Feng Q., Li X., Huang H., Wang S., Ji F., Jiang G. Copper-Catalyzed Divergent C–H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines // Organic Letters. 2022. Vol. 24. No. 9. pp. 1859-1864.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.2c00454

UR - https://doi.org/10.1021/acs.orglett.2c00454

TI - Copper-Catalyzed Divergent C–H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines

T2 - Organic Letters

AU - Yang, Guang

AU - Xiong, Zhicheng

AU - Nie, Hongsheng

AU - He, Meiqin

AU - Feng, Qiong

AU - Li, Xuan

AU - Huang, Huabin

AU - Wang, Shoucai

AU - Ji, Fanghua

AU - Jiang, Guangbin

PY - 2022

DA - 2022/02/28

PB - American Chemical Society (ACS)

SP - 1859-1864

IS - 9

VL - 24

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

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BibTex Copy

@article{2022_Yang,

author = {Guang Yang and Zhicheng Xiong and Hongsheng Nie and Meiqin He and Qiong Feng and Xuan Li and Huabin Huang and Shoucai Wang and Fanghua Ji and Guangbin Jiang},

title = {Copper-Catalyzed Divergent C–H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines},

journal = {Organic Letters},

year = {2022},

volume = {24},

publisher = {American Chemical Society (ACS)},

month = {feb},

url = {https://doi.org/10.1021/acs.orglett.2c00454},

number = {9},

pages = {1859--1864},

doi = {10.1021/acs.orglett.2c00454}

}

MLA

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MLA Copy

Yang, Guang, et al. “Copper-Catalyzed Divergent C–H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines.” Organic Letters, vol. 24, no. 9, Feb. 2022, pp. 1859-1864. https://doi.org/10.1021/acs.orglett.2c00454.

Found error?

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

Quartile SCImago

Quartile WOS

Impact factor

5.2

ISSN

15237060 (Print)
15237052 (Electronic)