Desymmetric [3+3] Cyclization of p‑Quinamines for the Synthesis of 1,2,4-Oxadiazines and Hydroquinoxalines

General and efficient strategies for highly diastereoselective synthesis of divergent heterocyclic scaffolds through desymmetric [3+3] cycloaddition of p-quinamines with 1,3-dipole surrogates hydroximoyl halides and α-halohydroxamates have been developed. This synthetic protocol provided a variety o...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2024-03, Vol.26 (9), p.1770-1774
Hauptverfasser: Wang, Xuerui, Ren, Weiwu
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1774
container_issue 9
container_start_page 1770
container_title Organic letters
container_volume 26
creator Wang, Xuerui
Ren, Weiwu
description General and efficient strategies for highly diastereoselective synthesis of divergent heterocyclic scaffolds through desymmetric [3+3] cycloaddition of p-quinamines with 1,3-dipole surrogates hydroximoyl halides and α-halohydroxamates have been developed. This synthetic protocol provided a variety of heterocyclic architectures containing 1,2,4-oxadiazine and hydroquinoxaline skeletons in good yields with a wide substrate scope.
doi_str_mv 10.1021/acs.orglett.3c04157
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2926520675</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2926520675</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-ae80ab58f56a60bd3d02b11d65bc3461cfc5293281fa5e9f6f4eeedfeb270e473</originalsourceid><addsrcrecordid>eNp9kNtKxDAQhoMoHlafQJBeCm7XHJq2eynrERYWUa9EQppONNI2a9KFrVe-gq_ok5i6q5dezTB8_wzzIXRI8IhgSk6l8iPrnito2xFTOCE820C7hFMWZ5jTzb8-xTtoz_tXjEmYjLfRDssZZ0lOdlF1Dr6ra2idUdEjO2FP0aRTlXmXrbFNZHU0__r4vF2YRtamAR9p66L2BaK7rgnFG98zZEiHSTxbytLI9x9MNmV03ZXOvoWoXcqqn-6jLS0rDwfrOkAPlxf3k-t4Oru6mZxNY8kS3sYSciwLnmueyhQXJSsxLQgpU14olqREaRXeYDQnWnIY61QnAFBqKGiGIcnYAB2v9s77--BbURuvoKpkA3bhBR3TlFOcZjygbIUqZ713oMXcmVq6ThAses0iaBZrzWKtOaSO1gcWRQ3lX-bXawBOV0CffrUL14R__135DeYMjh4</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2926520675</pqid></control><display><type>article</type><title>Desymmetric [3+3] Cyclization of p‑Quinamines for the Synthesis of 1,2,4-Oxadiazines and Hydroquinoxalines</title><source>American Chemical Society Journals</source><creator>Wang, Xuerui ; Ren, Weiwu</creator><creatorcontrib>Wang, Xuerui ; Ren, Weiwu</creatorcontrib><description>General and efficient strategies for highly diastereoselective synthesis of divergent heterocyclic scaffolds through desymmetric [3+3] cycloaddition of p-quinamines with 1,3-dipole surrogates hydroximoyl halides and α-halohydroxamates have been developed. This synthetic protocol provided a variety of heterocyclic architectures containing 1,2,4-oxadiazine and hydroquinoxaline skeletons in good yields with a wide substrate scope.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.3c04157</identifier><identifier>PMID: 38353481</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2024-03, Vol.26 (9), p.1770-1774</ispartof><rights>2024 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-ae80ab58f56a60bd3d02b11d65bc3461cfc5293281fa5e9f6f4eeedfeb270e473</citedby><cites>FETCH-LOGICAL-a345t-ae80ab58f56a60bd3d02b11d65bc3461cfc5293281fa5e9f6f4eeedfeb270e473</cites><orcidid>0000-0002-9485-1679</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.3c04157$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.3c04157$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38353481$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Xuerui</creatorcontrib><creatorcontrib>Ren, Weiwu</creatorcontrib><title>Desymmetric [3+3] Cyclization of p‑Quinamines for the Synthesis of 1,2,4-Oxadiazines and Hydroquinoxalines</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>General and efficient strategies for highly diastereoselective synthesis of divergent heterocyclic scaffolds through desymmetric [3+3] cycloaddition of p-quinamines with 1,3-dipole surrogates hydroximoyl halides and α-halohydroxamates have been developed. This synthetic protocol provided a variety of heterocyclic architectures containing 1,2,4-oxadiazine and hydroquinoxaline skeletons in good yields with a wide substrate scope.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp9kNtKxDAQhoMoHlafQJBeCm7XHJq2eynrERYWUa9EQppONNI2a9KFrVe-gq_ok5i6q5dezTB8_wzzIXRI8IhgSk6l8iPrnito2xFTOCE820C7hFMWZ5jTzb8-xTtoz_tXjEmYjLfRDssZZ0lOdlF1Dr6ra2idUdEjO2FP0aRTlXmXrbFNZHU0__r4vF2YRtamAR9p66L2BaK7rgnFG98zZEiHSTxbytLI9x9MNmV03ZXOvoWoXcqqn-6jLS0rDwfrOkAPlxf3k-t4Oru6mZxNY8kS3sYSciwLnmueyhQXJSsxLQgpU14olqREaRXeYDQnWnIY61QnAFBqKGiGIcnYAB2v9s77--BbURuvoKpkA3bhBR3TlFOcZjygbIUqZ713oMXcmVq6ThAses0iaBZrzWKtOaSO1gcWRQ3lX-bXawBOV0CffrUL14R__135DeYMjh4</recordid><startdate>20240308</startdate><enddate>20240308</enddate><creator>Wang, Xuerui</creator><creator>Ren, Weiwu</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-9485-1679</orcidid></search><sort><creationdate>20240308</creationdate><title>Desymmetric [3+3] Cyclization of p‑Quinamines for the Synthesis of 1,2,4-Oxadiazines and Hydroquinoxalines</title><author>Wang, Xuerui ; Ren, Weiwu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-ae80ab58f56a60bd3d02b11d65bc3461cfc5293281fa5e9f6f4eeedfeb270e473</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Xuerui</creatorcontrib><creatorcontrib>Ren, Weiwu</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>Wang, Xuerui</au><au>Ren, Weiwu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Desymmetric [3+3] Cyclization of p‑Quinamines for the Synthesis of 1,2,4-Oxadiazines and Hydroquinoxalines</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2024-03-08</date><risdate>2024</risdate><volume>26</volume><issue>9</issue><spage>1770</spage><epage>1774</epage><pages>1770-1774</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>General and efficient strategies for highly diastereoselective synthesis of divergent heterocyclic scaffolds through desymmetric [3+3] cycloaddition of p-quinamines with 1,3-dipole surrogates hydroximoyl halides and α-halohydroxamates have been developed. This synthetic protocol provided a variety of heterocyclic architectures containing 1,2,4-oxadiazine and hydroquinoxaline skeletons in good yields with a wide substrate scope.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>38353481</pmid><doi>10.1021/acs.orglett.3c04157</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-9485-1679</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2024-03, Vol.26 (9), p.1770-1774
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2926520675
source American Chemical Society Journals
title Desymmetric [3+3] Cyclization of p‑Quinamines for the Synthesis of 1,2,4-Oxadiazines and Hydroquinoxalines
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-01T07%3A42%3A01IST&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=Desymmetric%20%5B3+3%5D%20Cyclization%20of%20p%E2%80%91Quinamines%20for%20the%20Synthesis%20of%201,2,4-Oxadiazines%20and%20Hydroquinoxalines&rft.jtitle=Organic%20letters&rft.au=Wang,%20Xuerui&rft.date=2024-03-08&rft.volume=26&rft.issue=9&rft.spage=1770&rft.epage=1774&rft.pages=1770-1774&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.3c04157&rft_dat=%3Cproquest_cross%3E2926520675%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=2926520675&rft_id=info:pmid/38353481&rfr_iscdi=true