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
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 conditi...
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| Veröffentlicht in: | Organic letters 2022-03, Vol.24 (9), p.1859-1864 |
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| creator | Yang, Guang Xiong, Zhicheng Nie, Hongsheng He, Meiqin Feng, Qiong Li, Xuan Huang, Huabin Wang, Shoucai Ji, Fanghua Jiang, Guangbin |
| description | 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. |
| doi_str_mv | 10.1021/acs.orglett.2c00454 |
| format | Article |
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This new protocol features mild reaction conditions, readily available materials, and a broad substrate scope. Gram-scale and mechanistic studies were also investigated. 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Lett</addtitle><description>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.</description><subject>Alkynes</subject><subject>Catalysis</subject><subject>Copper</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Molecular Structure</subject><subject>Quinoxalines - pharmacology</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kcFu1DAQhiNERUvhCZCQj4tEtmMnzmaPVdplkapWULiAUOTYk5Litbe2g0hPfQXEK_EkfZI67HaPnObXzD_ff_iT5BWFKQVGj4T0U-uuNIYwZRIg5_mT5IBylqUz4OzpThewnzz3_hqAxs38WbKfccZ4wWYHyd_Krtfo0koEoYdbVOSk-4nuCk0g1f3dnyVZ9EaGzhqhu1sxCvIRxb8NsS350HfG_oo3k7IJXb65v_ttDXoijCLH-scw6sqa4KzWEd4M5Jyml33jQxf6GOJJax0J35FcDiYO3_kRO_kykk6NWEX8I2_RO_uVvc3ipfl2swtG_yLZa4X2-HI7D5PPi9NP1TI9u3j3vjo-S0WW85ByFLlqAZoMC8SiyRQobOYUeMbn0MiyzEFxxZAzWc5KyIVEYDOFEgquSpkdJpMNd-3sTY8-1KvOS9RaGLS9r1kRc2gORR6t2cYqnfXeYVuvXbcSbqgp1GN9dayv3tZXb-uLX6-3AX2zQrX7eewrGo42hvH72vYu1uL_i3wAbvCwog</recordid><startdate>20220311</startdate><enddate>20220311</enddate><creator>Yang, Guang</creator><creator>Xiong, Zhicheng</creator><creator>Nie, Hongsheng</creator><creator>He, Meiqin</creator><creator>Feng, Qiong</creator><creator>Li, Xuan</creator><creator>Huang, Huabin</creator><creator>Wang, Shoucai</creator><creator>Ji, Fanghua</creator><creator>Jiang, Guangbin</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7329-8854</orcidid><orcidid>https://orcid.org/0000-0002-5546-1942</orcidid><orcidid>https://orcid.org/0000-0003-1706-7570</orcidid><orcidid>https://orcid.org/0000-0001-8072-3425</orcidid><orcidid>https://orcid.org/0000-0002-9738-8309</orcidid><orcidid>https://orcid.org/0000-0002-8840-4741</orcidid><orcidid>https://orcid.org/0000-0002-6295-8842</orcidid><orcidid>https://orcid.org/0000-0002-2101-3930</orcidid><orcidid>https://orcid.org/0000-0002-2552-5618</orcidid><orcidid>https://orcid.org/0000-0002-7318-8388</orcidid></search><sort><creationdate>20220311</creationdate><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</title><author>Yang, Guang ; Xiong, Zhicheng ; Nie, Hongsheng ; He, Meiqin ; Feng, Qiong ; Li, Xuan ; Huang, Huabin ; Wang, Shoucai ; Ji, Fanghua ; Jiang, Guangbin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-5ea4df00b3e6ee6b3d0deb91053590bc8840d5d2e52c87804ace027dec065d8c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkynes</topic><topic>Catalysis</topic><topic>Copper</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Molecular Structure</topic><topic>Quinoxalines - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Guang</creatorcontrib><creatorcontrib>Xiong, Zhicheng</creatorcontrib><creatorcontrib>Nie, Hongsheng</creatorcontrib><creatorcontrib>He, Meiqin</creatorcontrib><creatorcontrib>Feng, Qiong</creatorcontrib><creatorcontrib>Li, Xuan</creatorcontrib><creatorcontrib>Huang, Huabin</creatorcontrib><creatorcontrib>Wang, Shoucai</creatorcontrib><creatorcontrib>Ji, Fanghua</creatorcontrib><creatorcontrib>Jiang, Guangbin</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Guang</au><au>Xiong, Zhicheng</au><au>Nie, Hongsheng</au><au>He, Meiqin</au><au>Feng, Qiong</au><au>Li, Xuan</au><au>Huang, Huabin</au><au>Wang, Shoucai</au><au>Ji, Fanghua</au><au>Jiang, Guangbin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>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</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2022-03-11</date><risdate>2022</risdate><volume>24</volume><issue>9</issue><spage>1859</spage><epage>1864</epage><pages>1859-1864</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><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. 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| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkynes Catalysis Copper HeLa Cells Humans Molecular Structure Quinoxalines - pharmacology |
| 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 |
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