Metal‐ and Base‐Free Radical Cascade Cyclization/Hydrolysis of CN‐Containing 1,6‐Enynes with Ethers to Access Polyheterocycles
A convenient and straightforward approach for the radical cascade cyclization/hydrolysis of CN‐containing 1,6‐enynes with simple ethers under metal‐ and base‐free conditions is described. This strategy provides a variety of valuable ethers‐substituted polyheterocycles via the construction of three C...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2023-02, Vol.18 (3), p.e202201149-n/a |
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| container_title | Chemistry, an Asian journal |
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| creator | Zheng, Yan‐Nan Cai, Xue‐Er Wu, Hong‐Li Zhou, Yu Tian, Wen‐Chan Ruan, Yiping Liu, Hongxin Wei, Wen‐Ting |
| description | A convenient and straightforward approach for the radical cascade cyclization/hydrolysis of CN‐containing 1,6‐enynes with simple ethers under metal‐ and base‐free conditions is described. This strategy provides a variety of valuable ethers‐substituted polyheterocycles via the construction of three C−C bonds, one C=O bond, and two new six‐membered rings within a single procedure. The resulting products can smoothly undergo follow‐up conversions to various useful scaffolds. The methodology shows excellent functional group tolerance, high step‐ and atom‐ economy, and mild reaction conditions, which can be further scaled up to gram quantity in a satisfactory yield.
A novel method for preparing polyheterocycles from CN‐containing 1,6‐enynes with ethers via a metal‐ and base‐free radical cascade cyclization/hydrolysis reaction has been established. |
| doi_str_mv | 10.1002/asia.202201149 |
| format | Article |
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A novel method for preparing polyheterocycles from CN‐containing 1,6‐enynes with ethers via a metal‐ and base‐free radical cascade cyclization/hydrolysis reaction has been established.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.202201149</identifier><identifier>PMID: 36550634</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Base-free ; cascade cyclization ; Chemistry ; CN-containing 1,6-enynes ; Ethers ; Free radicals ; Functional groups ; green synthesis ; Hydrolysis ; metal-free</subject><ispartof>Chemistry, an Asian journal, 2023-02, Vol.18 (3), p.e202201149-n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><rights>2022 Wiley-VCH GmbH.</rights><rights>2023 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3739-6f133d58b069862da9366d85b7fea8b8416073d30861abf3542aabd3845da3003</citedby><cites>FETCH-LOGICAL-c3739-6f133d58b069862da9366d85b7fea8b8416073d30861abf3542aabd3845da3003</cites><orcidid>0000-0001-7942-8656</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fasia.202201149$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.202201149$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36550634$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zheng, Yan‐Nan</creatorcontrib><creatorcontrib>Cai, Xue‐Er</creatorcontrib><creatorcontrib>Wu, Hong‐Li</creatorcontrib><creatorcontrib>Zhou, Yu</creatorcontrib><creatorcontrib>Tian, Wen‐Chan</creatorcontrib><creatorcontrib>Ruan, Yiping</creatorcontrib><creatorcontrib>Liu, Hongxin</creatorcontrib><creatorcontrib>Wei, Wen‐Ting</creatorcontrib><title>Metal‐ and Base‐Free Radical Cascade Cyclization/Hydrolysis of CN‐Containing 1,6‐Enynes with Ethers to Access Polyheterocycles</title><title>Chemistry, an Asian journal</title><addtitle>Chem Asian J</addtitle><description>A convenient and straightforward approach for the radical cascade cyclization/hydrolysis of CN‐containing 1,6‐enynes with simple ethers under metal‐ and base‐free conditions is described. This strategy provides a variety of valuable ethers‐substituted polyheterocycles via the construction of three C−C bonds, one C=O bond, and two new six‐membered rings within a single procedure. The resulting products can smoothly undergo follow‐up conversions to various useful scaffolds. The methodology shows excellent functional group tolerance, high step‐ and atom‐ economy, and mild reaction conditions, which can be further scaled up to gram quantity in a satisfactory yield.
A novel method for preparing polyheterocycles from CN‐containing 1,6‐enynes with ethers via a metal‐ and base‐free radical cascade cyclization/hydrolysis reaction has been established.</description><subject>Base-free</subject><subject>cascade cyclization</subject><subject>Chemistry</subject><subject>CN-containing 1,6-enynes</subject><subject>Ethers</subject><subject>Free radicals</subject><subject>Functional groups</subject><subject>green synthesis</subject><subject>Hydrolysis</subject><subject>metal-free</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkTtvFDEURkcIREJCS4ks0VCwGz_GHk-5jDYPKTwUQKIb3bHvsI5m7cSeVTSpUqXmN_JLcLRhkWiofGWd7_haX1G8YnTOKOVHkBzMOeWcMlbWT4p9phWblRX7_nQ3c71XvEjpklLJaa2fF3tCSUmVKPeL-w84wvDr7icBb8l7SJjn44hILsA6AwNpIBmwSJrJDO4WRhf80elkYxim5BIJPWk-5kwT_AjOO_-DsHcqXyz95DGRGzeuyHJcYUxkDGRhDKZEPuf0CkeMwWQtpsPiWQ9DwpeP50Hx7Xj5tTmdnX86OWsW5zMjKlHPVM-EsFJ3VNVacQu1UMpq2VU9gu50yRSthBU0fxy6XsiSA3RW6FJaEJSKg-Lt1nsVw_UG09iuXTI4DOAxbFLLK6kZrfNbGX3zD3oZNtHn7TJViUqWrFaZmm8pE0NKEfv2Kro1xKlltH1oqH1oqN01lAOvH7Wbbo12h_-pJAP1FrhxA07_0bWLL2eLv_LfPMKgPg</recordid><startdate>20230201</startdate><enddate>20230201</enddate><creator>Zheng, Yan‐Nan</creator><creator>Cai, Xue‐Er</creator><creator>Wu, Hong‐Li</creator><creator>Zhou, Yu</creator><creator>Tian, Wen‐Chan</creator><creator>Ruan, Yiping</creator><creator>Liu, Hongxin</creator><creator>Wei, Wen‐Ting</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7942-8656</orcidid></search><sort><creationdate>20230201</creationdate><title>Metal‐ and Base‐Free Radical Cascade Cyclization/Hydrolysis of CN‐Containing 1,6‐Enynes with Ethers to Access Polyheterocycles</title><author>Zheng, Yan‐Nan ; Cai, Xue‐Er ; Wu, Hong‐Li ; Zhou, Yu ; Tian, Wen‐Chan ; Ruan, Yiping ; Liu, Hongxin ; Wei, Wen‐Ting</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3739-6f133d58b069862da9366d85b7fea8b8416073d30861abf3542aabd3845da3003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Base-free</topic><topic>cascade cyclization</topic><topic>Chemistry</topic><topic>CN-containing 1,6-enynes</topic><topic>Ethers</topic><topic>Free radicals</topic><topic>Functional groups</topic><topic>green synthesis</topic><topic>Hydrolysis</topic><topic>metal-free</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zheng, Yan‐Nan</creatorcontrib><creatorcontrib>Cai, Xue‐Er</creatorcontrib><creatorcontrib>Wu, Hong‐Li</creatorcontrib><creatorcontrib>Zhou, Yu</creatorcontrib><creatorcontrib>Tian, Wen‐Chan</creatorcontrib><creatorcontrib>Ruan, Yiping</creatorcontrib><creatorcontrib>Liu, Hongxin</creatorcontrib><creatorcontrib>Wei, Wen‐Ting</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zheng, Yan‐Nan</au><au>Cai, Xue‐Er</au><au>Wu, Hong‐Li</au><au>Zhou, Yu</au><au>Tian, Wen‐Chan</au><au>Ruan, Yiping</au><au>Liu, Hongxin</au><au>Wei, Wen‐Ting</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metal‐ and Base‐Free Radical Cascade Cyclization/Hydrolysis of CN‐Containing 1,6‐Enynes with Ethers to Access Polyheterocycles</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chem Asian J</addtitle><date>2023-02-01</date><risdate>2023</risdate><volume>18</volume><issue>3</issue><spage>e202201149</spage><epage>n/a</epage><pages>e202201149-n/a</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>A convenient and straightforward approach for the radical cascade cyclization/hydrolysis of CN‐containing 1,6‐enynes with simple ethers under metal‐ and base‐free conditions is described. This strategy provides a variety of valuable ethers‐substituted polyheterocycles via the construction of three C−C bonds, one C=O bond, and two new six‐membered rings within a single procedure. The resulting products can smoothly undergo follow‐up conversions to various useful scaffolds. The methodology shows excellent functional group tolerance, high step‐ and atom‐ economy, and mild reaction conditions, which can be further scaled up to gram quantity in a satisfactory yield.
A novel method for preparing polyheterocycles from CN‐containing 1,6‐enynes with ethers via a metal‐ and base‐free radical cascade cyclization/hydrolysis reaction has been established.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>36550634</pmid><doi>10.1002/asia.202201149</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-7942-8656</orcidid></addata></record> |
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| subjects | Base-free cascade cyclization Chemistry CN-containing 1,6-enynes Ethers Free radicals Functional groups green synthesis Hydrolysis metal-free |
| title | Metal‐ and Base‐Free Radical Cascade Cyclization/Hydrolysis of CN‐Containing 1,6‐Enynes with Ethers to Access Polyheterocycles |
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