Highly Regioselective and Chemoselective [3 + 3] Annulation of Enaminones with ortho-Fluoronitrobenzenenes: Divergent Synthesis of Aposafranones and Their N‑Oxides
A base-promoted unprecedented strategy for the regioselective and chemoselective divergent synthesis of highly functionalized aposafranones and their N-oxides has been developed from the [3 + 3] annulation of enaminones with o-fluoronitrobenzenenes. This novel synthetic strategy offers an alternativ...
Gespeichert in:
Veröffentlicht in: | Organic letters 2021-04, Vol.23 (8), p.3032-3037 |
---|---|
Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 3037 |
---|---|
container_issue | 8 |
container_start_page | 3032 |
container_title | Organic letters |
container_volume | 23 |
creator | Chen, Xue-Bing Huang, Shun-Tao Li, Jie Yang, Qi Yang, Li Yu, Fuchao |
description | A base-promoted unprecedented strategy for the regioselective and chemoselective divergent synthesis of highly functionalized aposafranones and their N-oxides has been developed from the [3 + 3] annulation of enaminones with o-fluoronitrobenzenenes. This novel synthetic strategy offers an alternative method for the construction of aposafranones and their N-oxides are meaningful in the fields of both biology and organic synthesis. The established protocol explores the annulation scope of enaminones, and it expands the application of nitro-based cyclization. |
doi_str_mv | 10.1021/acs.orglett.1c00710 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2507733415</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2507733415</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-7fe73990704b6ab9fc102e99644d0a311d3b7720746804576b32b3585d48af1c3</originalsourceid><addsrcrecordid>eNp9kdtKxDAQhoMoHlafQJBcCtLdpGmbrXfLegRR8HAlUtJ2uo20yZqk6nrlK_gQvphPYpZdxSvJxYTh__9h5kNol5I-JSEdiML2tZk04FyfFoRwSlbQJo1DFnASh6u__4RsoC1rHwmhvpOuow3GeBqyiG6izzM5qZsZvoaJ1BYaKJx8BixUicc1tH9a9wwfYPaAR0p1jXBSK6wrfKxEK5VWYPGLdDXWxtU6OGk6bbSSzugc1Bso_-whPvI5ZgLK4ZuZcjVYaecZo6m2ojJiETMffVuDNPjy6_3j6lWWYLfRWiUaCzvL2kN3J8e347Pg4ur0fDy6CASLYhfwCjhLU8JJlCciT6vCHwrSNImikghGaclyzkPCo2RIopgnOQtzFg_jMhqKihash_YXuVOjnzqwLmulLaBphALd2SyMCefMHy72UraQFkZba6DKpka2wswySrI5n8zzyZZ8siUf79pbDujyFspfzw8QLxgsBHP3o-6M8vv-G_kNv5GiFw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2507733415</pqid></control><display><type>article</type><title>Highly Regioselective and Chemoselective [3 + 3] Annulation of Enaminones with ortho-Fluoronitrobenzenenes: Divergent Synthesis of Aposafranones and Their N‑Oxides</title><source>American Chemical Society Journals</source><creator>Chen, Xue-Bing ; Huang, Shun-Tao ; Li, Jie ; Yang, Qi ; Yang, Li ; Yu, Fuchao</creator><creatorcontrib>Chen, Xue-Bing ; Huang, Shun-Tao ; Li, Jie ; Yang, Qi ; Yang, Li ; Yu, Fuchao</creatorcontrib><description>A base-promoted unprecedented strategy for the regioselective and chemoselective divergent synthesis of highly functionalized aposafranones and their N-oxides has been developed from the [3 + 3] annulation of enaminones with o-fluoronitrobenzenenes. This novel synthetic strategy offers an alternative method for the construction of aposafranones and their N-oxides are meaningful in the fields of both biology and organic synthesis. The established protocol explores the annulation scope of enaminones, and it expands the application of nitro-based cyclization.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.1c00710</identifier><identifier>PMID: 33792341</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2021-04, Vol.23 (8), p.3032-3037</ispartof><rights>2021 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-7fe73990704b6ab9fc102e99644d0a311d3b7720746804576b32b3585d48af1c3</citedby><cites>FETCH-LOGICAL-a345t-7fe73990704b6ab9fc102e99644d0a311d3b7720746804576b32b3585d48af1c3</cites><orcidid>0000-0002-1936-1274 ; 0000-0001-5557-3824</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.1c00710$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.1c00710$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27063,27911,27912,56725,56775</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33792341$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Xue-Bing</creatorcontrib><creatorcontrib>Huang, Shun-Tao</creatorcontrib><creatorcontrib>Li, Jie</creatorcontrib><creatorcontrib>Yang, Qi</creatorcontrib><creatorcontrib>Yang, Li</creatorcontrib><creatorcontrib>Yu, Fuchao</creatorcontrib><title>Highly Regioselective and Chemoselective [3 + 3] Annulation of Enaminones with ortho-Fluoronitrobenzenenes: Divergent Synthesis of Aposafranones and Their N‑Oxides</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A base-promoted unprecedented strategy for the regioselective and chemoselective divergent synthesis of highly functionalized aposafranones and their N-oxides has been developed from the [3 + 3] annulation of enaminones with o-fluoronitrobenzenenes. This novel synthetic strategy offers an alternative method for the construction of aposafranones and their N-oxides are meaningful in the fields of both biology and organic synthesis. The established protocol explores the annulation scope of enaminones, and it expands the application of nitro-based cyclization.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kdtKxDAQhoMoHlafQJBcCtLdpGmbrXfLegRR8HAlUtJ2uo20yZqk6nrlK_gQvphPYpZdxSvJxYTh__9h5kNol5I-JSEdiML2tZk04FyfFoRwSlbQJo1DFnASh6u__4RsoC1rHwmhvpOuow3GeBqyiG6izzM5qZsZvoaJ1BYaKJx8BixUicc1tH9a9wwfYPaAR0p1jXBSK6wrfKxEK5VWYPGLdDXWxtU6OGk6bbSSzugc1Bso_-whPvI5ZgLK4ZuZcjVYaecZo6m2ojJiETMffVuDNPjy6_3j6lWWYLfRWiUaCzvL2kN3J8e347Pg4ur0fDy6CASLYhfwCjhLU8JJlCciT6vCHwrSNImikghGaclyzkPCo2RIopgnOQtzFg_jMhqKihash_YXuVOjnzqwLmulLaBphALd2SyMCefMHy72UraQFkZba6DKpka2wswySrI5n8zzyZZ8siUf79pbDujyFspfzw8QLxgsBHP3o-6M8vv-G_kNv5GiFw</recordid><startdate>20210416</startdate><enddate>20210416</enddate><creator>Chen, Xue-Bing</creator><creator>Huang, Shun-Tao</creator><creator>Li, Jie</creator><creator>Yang, Qi</creator><creator>Yang, Li</creator><creator>Yu, Fuchao</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1936-1274</orcidid><orcidid>https://orcid.org/0000-0001-5557-3824</orcidid></search><sort><creationdate>20210416</creationdate><title>Highly Regioselective and Chemoselective [3 + 3] Annulation of Enaminones with ortho-Fluoronitrobenzenenes: Divergent Synthesis of Aposafranones and Their N‑Oxides</title><author>Chen, Xue-Bing ; Huang, Shun-Tao ; Li, Jie ; Yang, Qi ; Yang, Li ; Yu, Fuchao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-7fe73990704b6ab9fc102e99644d0a311d3b7720746804576b32b3585d48af1c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Xue-Bing</creatorcontrib><creatorcontrib>Huang, Shun-Tao</creatorcontrib><creatorcontrib>Li, Jie</creatorcontrib><creatorcontrib>Yang, Qi</creatorcontrib><creatorcontrib>Yang, Li</creatorcontrib><creatorcontrib>Yu, Fuchao</creatorcontrib><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>Chen, Xue-Bing</au><au>Huang, Shun-Tao</au><au>Li, Jie</au><au>Yang, Qi</au><au>Yang, Li</au><au>Yu, Fuchao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly Regioselective and Chemoselective [3 + 3] Annulation of Enaminones with ortho-Fluoronitrobenzenenes: Divergent Synthesis of Aposafranones and Their N‑Oxides</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2021-04-16</date><risdate>2021</risdate><volume>23</volume><issue>8</issue><spage>3032</spage><epage>3037</epage><pages>3032-3037</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A base-promoted unprecedented strategy for the regioselective and chemoselective divergent synthesis of highly functionalized aposafranones and their N-oxides has been developed from the [3 + 3] annulation of enaminones with o-fluoronitrobenzenenes. This novel synthetic strategy offers an alternative method for the construction of aposafranones and their N-oxides are meaningful in the fields of both biology and organic synthesis. The established protocol explores the annulation scope of enaminones, and it expands the application of nitro-based cyclization.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>33792341</pmid><doi>10.1021/acs.orglett.1c00710</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-1936-1274</orcidid><orcidid>https://orcid.org/0000-0001-5557-3824</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1523-7060 |
ispartof | Organic letters, 2021-04, Vol.23 (8), p.3032-3037 |
issn | 1523-7060 1523-7052 |
language | eng |
recordid | cdi_proquest_miscellaneous_2507733415 |
source | American Chemical Society Journals |
title | Highly Regioselective and Chemoselective [3 + 3] Annulation of Enaminones with ortho-Fluoronitrobenzenenes: Divergent Synthesis of Aposafranones and Their N‑Oxides |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-15T16%3A11%3A12IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Highly%20Regioselective%20and%20Chemoselective%20%5B3%20+%203%5D%20Annulation%20of%20Enaminones%20with%20ortho-Fluoronitrobenzenenes:%20Divergent%20Synthesis%20of%20Aposafranones%20and%20Their%20N%E2%80%91Oxides&rft.jtitle=Organic%20letters&rft.au=Chen,%20Xue-Bing&rft.date=2021-04-16&rft.volume=23&rft.issue=8&rft.spage=3032&rft.epage=3037&rft.pages=3032-3037&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.1c00710&rft_dat=%3Cproquest_cross%3E2507733415%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2507733415&rft_id=info:pmid/33792341&rfr_iscdi=true |