A Cascade Rh(III)‐catalyzed C−H Activation/Chemodivergent Annulation of N‐carbamoylindoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone and Tricyclic [1,3]Oxazino[3,4‐a]indol‐1‐ones Derivatives
A highly efficient cascade Rh(III)‐catalyzed C−H activation/intramolecular chemodivergent cyclization reaction of N‐carbamoylindoles and sulfoxonium ylides has been successfully achieved for the first time. This synergistic process provides rapid access to functionalized dihydropyrimidoindolone and...
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Veröffentlicht in: | Advanced synthesis & catalysis 2021-03, Vol.363 (5), p.1436-1442 |
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creator | Xie, Hui Zhong, Mei Kang, Hua‐Jie Shu, Bing Zhang, Shang‐Shi |
description | A highly efficient cascade Rh(III)‐catalyzed C−H activation/intramolecular chemodivergent cyclization reaction of N‐carbamoylindoles and sulfoxonium ylides has been successfully achieved for the first time. This synergistic process provides rapid access to functionalized dihydropyrimidoindolone and tricyclic [1,3]oxazino[3,4‐a]indol‐1‐ones skeletons under redox neutral conditions with broad substrate scope and remarkable functional‐group compatibility. Further late‐stage modification of structurally complex drug molecules and mechanistic studies were also accomplished. |
doi_str_mv | 10.1002/adsc.202001380 |
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Further late‐stage modification of structurally complex drug molecules and mechanistic studies were also accomplished.</description><subject>annulation</subject><subject>cascade</subject><subject>N-carbamoylindoles</subject><subject>Rh(III)-catalyzed</subject><subject>sulfoxonium ylides</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFUU1LxDAULKLg59VzjgrumjTttj2Wrh8LouDqQUTK2yS1kWwiSXfdevLoUfyJgv_DbBU9eghvyJuZl5cJgl2C-wTj8BC4Y_0QhxgTmuKVYIMMSNyLyCBb_cUxXg82nXvwnCRNko3gM0cFOAZcoMt6bzQa7X-8vDFoQLXPgqPi4_X9FOWskXNopNGHRS2mhsu5sPdCNyjXeqa6DjIVOu-0dgJT0yqpuVHCoSfZ1Gg8U5VZGC1nU3SjJPf3lbGoqQUat9oXJ93SYSjrllvz2Fo5ldx0HkYLBJqjKytZy5Rk6JYc0LuLBTxLbW7pQeTHwl3H9Yj44yUODYXtXj0XbjtYq0A5sfNTt4Lr46Or4rR3dnEyKvKzHqPhAPeApzHAIIMsYyFjgGOGaQgZjXDCcIUnUSqSpErCSEw8inmEYxrHqf_ihFOgdCvof_sya5yzoiof_SJg25LgchlSuQyp_A3JC7JvwZNUov2HXebDcfGn_QLLqKD6</recordid><startdate>20210302</startdate><enddate>20210302</enddate><creator>Xie, Hui</creator><creator>Zhong, Mei</creator><creator>Kang, Hua‐Jie</creator><creator>Shu, Bing</creator><creator>Zhang, Shang‐Shi</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-9247-1373</orcidid></search><sort><creationdate>20210302</creationdate><title>A Cascade Rh(III)‐catalyzed C−H Activation/Chemodivergent Annulation of N‐carbamoylindoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone and Tricyclic [1,3]Oxazino[3,4‐a]indol‐1‐ones Derivatives</title><author>Xie, Hui ; Zhong, Mei ; Kang, Hua‐Jie ; Shu, Bing ; Zhang, Shang‐Shi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3260-ad85aa69a99c2cca05c032a93407c0f0b48e77f724eb8e75d40535581697d3a33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>annulation</topic><topic>cascade</topic><topic>N-carbamoylindoles</topic><topic>Rh(III)-catalyzed</topic><topic>sulfoxonium ylides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xie, Hui</creatorcontrib><creatorcontrib>Zhong, Mei</creatorcontrib><creatorcontrib>Kang, Hua‐Jie</creatorcontrib><creatorcontrib>Shu, Bing</creatorcontrib><creatorcontrib>Zhang, Shang‐Shi</creatorcontrib><collection>CrossRef</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xie, Hui</au><au>Zhong, Mei</au><au>Kang, Hua‐Jie</au><au>Shu, Bing</au><au>Zhang, Shang‐Shi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Cascade Rh(III)‐catalyzed C−H Activation/Chemodivergent Annulation of N‐carbamoylindoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone and Tricyclic [1,3]Oxazino[3,4‐a]indol‐1‐ones Derivatives</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2021-03-02</date><risdate>2021</risdate><volume>363</volume><issue>5</issue><spage>1436</spage><epage>1442</epage><pages>1436-1442</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A highly efficient cascade Rh(III)‐catalyzed C−H activation/intramolecular chemodivergent cyclization reaction of N‐carbamoylindoles and sulfoxonium ylides has been successfully achieved for the first time. This synergistic process provides rapid access to functionalized dihydropyrimidoindolone and tricyclic [1,3]oxazino[3,4‐a]indol‐1‐ones skeletons under redox neutral conditions with broad substrate scope and remarkable functional‐group compatibility. Further late‐stage modification of structurally complex drug molecules and mechanistic studies were also accomplished.</abstract><doi>10.1002/adsc.202001380</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-9247-1373</orcidid></addata></record> |
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subjects | annulation cascade N-carbamoylindoles Rh(III)-catalyzed sulfoxonium ylides |
title | A Cascade Rh(III)‐catalyzed C−H Activation/Chemodivergent Annulation of N‐carbamoylindoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone and Tricyclic [1,3]Oxazino[3,4‐a]indol‐1‐ones Derivatives |
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