[3+2] Cycloaddition of Rationally Designed Trisubstituted Cyclic α‐Chloroamide: an Alternative Strategy for Accessing Spirocyclic γ‐Lactam Architecture
Here we present a [3+2] cycloaddition of rationally designed trisubstituted cyclic α‐chloroamides, primarily those incorporating pharmacological pyrazolone cores, as potent synthons for synthesizing valuable spirocyclic γ‐lactam architectures. This protocol exhibits 52–96% yields, impressive substra...
Gespeichert in:
Veröffentlicht in: | Advanced synthesis & catalysis 2024-01, Vol.366 (2), p.269-276 |
---|---|
Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 276 |
---|---|
container_issue | 2 |
container_start_page | 269 |
container_title | Advanced synthesis & catalysis |
container_volume | 366 |
creator | Li, Yang Zuo, Wei‐Fang Chen, Jian‐Hua Li, Wei Zheng, Jinfeng Han, Bo Li, Xiang Huang, Wei |
description | Here we present a [3+2] cycloaddition of rationally designed trisubstituted cyclic α‐chloroamides, primarily those incorporating pharmacological pyrazolone cores, as potent synthons for synthesizing valuable spirocyclic γ‐lactam architectures. This protocol exhibits 52–96% yields, impressive substrate compatibility, and scale‐up capacity. Importantly, this study also represents one of the rare examples that harness enaminone C−N bond cleavage to engineer relevant spirocyclic γ‐lactam skeletons of biological interest. Moreover, we propose a plausible mechanistic explanation to elucidate the outstanding chemical outcomes observed, thereby enriching the synthetic toolbox for pyrazolone chemistry and α‐haloamide‐mediated reactions. |
doi_str_mv | 10.1002/adsc.202301175 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2919910857</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2919910857</sourcerecordid><originalsourceid>FETCH-LOGICAL-c2725-6d6ff179409f587667abc586107934e94fcfea1e40df61d6417a7e17974e89943</originalsourceid><addsrcrecordid>eNqFkU9Kw0AUh4MoWKtb1wMupXUmTWYy7kL8CwXB1pVImE7etFPSTJ2ZKNl5BC_gIcR7eAhPYkpLXbp678Hv-3jwC4JjgvsE4_BMFE72QxwOMCEs3gk6hJK4FxHKd7d7jPeDA-fmGBOWMNYJPh4Hp-ETyhpZGlEU2mtTIaPQvVhtoiwbdAFOTyso0NhqV0-c17727blitETfnz9v79msNNaIhS7gHIkKpaUHW7WOF0Ajb4WHaYOUsSiVEpzT1RSNltoauXF8tY6hkF4sUGrlTHuQvrZwGOwpUTo42sxu8HB1Oc5uesO769ssHfZkyMK4RwuqFGE8wlzFCaOUiYmME0ow44MIeKSkAkEgwoWipKARYYJBC7AIEs6jQTc4WXuX1jzX4Hw-N3X7f-nykBPOCU5i1qb665S0xjkLKl9avRC2yQnOVxXkqwrybQUtwNfAqy6h-Sedpxej7I_9BcfBkA8</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2919910857</pqid></control><display><type>article</type><title>[3+2] Cycloaddition of Rationally Designed Trisubstituted Cyclic α‐Chloroamide: an Alternative Strategy for Accessing Spirocyclic γ‐Lactam Architecture</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Li, Yang ; Zuo, Wei‐Fang ; Chen, Jian‐Hua ; Li, Wei ; Zheng, Jinfeng ; Han, Bo ; Li, Xiang ; Huang, Wei</creator><creatorcontrib>Li, Yang ; Zuo, Wei‐Fang ; Chen, Jian‐Hua ; Li, Wei ; Zheng, Jinfeng ; Han, Bo ; Li, Xiang ; Huang, Wei</creatorcontrib><description>Here we present a [3+2] cycloaddition of rationally designed trisubstituted cyclic α‐chloroamides, primarily those incorporating pharmacological pyrazolone cores, as potent synthons for synthesizing valuable spirocyclic γ‐lactam architectures. This protocol exhibits 52–96% yields, impressive substrate compatibility, and scale‐up capacity. Importantly, this study also represents one of the rare examples that harness enaminone C−N bond cleavage to engineer relevant spirocyclic γ‐lactam skeletons of biological interest. Moreover, we propose a plausible mechanistic explanation to elucidate the outstanding chemical outcomes observed, thereby enriching the synthetic toolbox for pyrazolone chemistry and α‐haloamide‐mediated reactions.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202301175</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Amides ; Cycloaddition ; Enaminone ; Pyrazolone ; Pyrazolones ; Spirocyclic Architecture ; Substrates ; α-Haloamide ; γ-Lactam</subject><ispartof>Advanced synthesis & catalysis, 2024-01, Vol.366 (2), p.269-276</ispartof><rights>2023 Wiley‐VCH GmbH</rights><rights>2024 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2725-6d6ff179409f587667abc586107934e94fcfea1e40df61d6417a7e17974e89943</cites><orcidid>0000-0003-0832-1864 ; 0000-0003-3200-4682</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%2Fadsc.202301175$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202301175$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Li, Yang</creatorcontrib><creatorcontrib>Zuo, Wei‐Fang</creatorcontrib><creatorcontrib>Chen, Jian‐Hua</creatorcontrib><creatorcontrib>Li, Wei</creatorcontrib><creatorcontrib>Zheng, Jinfeng</creatorcontrib><creatorcontrib>Han, Bo</creatorcontrib><creatorcontrib>Li, Xiang</creatorcontrib><creatorcontrib>Huang, Wei</creatorcontrib><title>[3+2] Cycloaddition of Rationally Designed Trisubstituted Cyclic α‐Chloroamide: an Alternative Strategy for Accessing Spirocyclic γ‐Lactam Architecture</title><title>Advanced synthesis & catalysis</title><description>Here we present a [3+2] cycloaddition of rationally designed trisubstituted cyclic α‐chloroamides, primarily those incorporating pharmacological pyrazolone cores, as potent synthons for synthesizing valuable spirocyclic γ‐lactam architectures. This protocol exhibits 52–96% yields, impressive substrate compatibility, and scale‐up capacity. Importantly, this study also represents one of the rare examples that harness enaminone C−N bond cleavage to engineer relevant spirocyclic γ‐lactam skeletons of biological interest. Moreover, we propose a plausible mechanistic explanation to elucidate the outstanding chemical outcomes observed, thereby enriching the synthetic toolbox for pyrazolone chemistry and α‐haloamide‐mediated reactions.</description><subject>Amides</subject><subject>Cycloaddition</subject><subject>Enaminone</subject><subject>Pyrazolone</subject><subject>Pyrazolones</subject><subject>Spirocyclic Architecture</subject><subject>Substrates</subject><subject>α-Haloamide</subject><subject>γ-Lactam</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkU9Kw0AUh4MoWKtb1wMupXUmTWYy7kL8CwXB1pVImE7etFPSTJ2ZKNl5BC_gIcR7eAhPYkpLXbp678Hv-3jwC4JjgvsE4_BMFE72QxwOMCEs3gk6hJK4FxHKd7d7jPeDA-fmGBOWMNYJPh4Hp-ETyhpZGlEU2mtTIaPQvVhtoiwbdAFOTyso0NhqV0-c17727blitETfnz9v79msNNaIhS7gHIkKpaUHW7WOF0Ajb4WHaYOUsSiVEpzT1RSNltoauXF8tY6hkF4sUGrlTHuQvrZwGOwpUTo42sxu8HB1Oc5uesO769ssHfZkyMK4RwuqFGE8wlzFCaOUiYmME0ow44MIeKSkAkEgwoWipKARYYJBC7AIEs6jQTc4WXuX1jzX4Hw-N3X7f-nykBPOCU5i1qb665S0xjkLKl9avRC2yQnOVxXkqwrybQUtwNfAqy6h-Sedpxej7I_9BcfBkA8</recordid><startdate>20240130</startdate><enddate>20240130</enddate><creator>Li, Yang</creator><creator>Zuo, Wei‐Fang</creator><creator>Chen, Jian‐Hua</creator><creator>Li, Wei</creator><creator>Zheng, Jinfeng</creator><creator>Han, Bo</creator><creator>Li, Xiang</creator><creator>Huang, Wei</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0003-0832-1864</orcidid><orcidid>https://orcid.org/0000-0003-3200-4682</orcidid></search><sort><creationdate>20240130</creationdate><title>[3+2] Cycloaddition of Rationally Designed Trisubstituted Cyclic α‐Chloroamide: an Alternative Strategy for Accessing Spirocyclic γ‐Lactam Architecture</title><author>Li, Yang ; Zuo, Wei‐Fang ; Chen, Jian‐Hua ; Li, Wei ; Zheng, Jinfeng ; Han, Bo ; Li, Xiang ; Huang, Wei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2725-6d6ff179409f587667abc586107934e94fcfea1e40df61d6417a7e17974e89943</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Amides</topic><topic>Cycloaddition</topic><topic>Enaminone</topic><topic>Pyrazolone</topic><topic>Pyrazolones</topic><topic>Spirocyclic Architecture</topic><topic>Substrates</topic><topic>α-Haloamide</topic><topic>γ-Lactam</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Yang</creatorcontrib><creatorcontrib>Zuo, Wei‐Fang</creatorcontrib><creatorcontrib>Chen, Jian‐Hua</creatorcontrib><creatorcontrib>Li, Wei</creatorcontrib><creatorcontrib>Zheng, Jinfeng</creatorcontrib><creatorcontrib>Han, Bo</creatorcontrib><creatorcontrib>Li, Xiang</creatorcontrib><creatorcontrib>Huang, Wei</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Yang</au><au>Zuo, Wei‐Fang</au><au>Chen, Jian‐Hua</au><au>Li, Wei</au><au>Zheng, Jinfeng</au><au>Han, Bo</au><au>Li, Xiang</au><au>Huang, Wei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>[3+2] Cycloaddition of Rationally Designed Trisubstituted Cyclic α‐Chloroamide: an Alternative Strategy for Accessing Spirocyclic γ‐Lactam Architecture</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2024-01-30</date><risdate>2024</risdate><volume>366</volume><issue>2</issue><spage>269</spage><epage>276</epage><pages>269-276</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Here we present a [3+2] cycloaddition of rationally designed trisubstituted cyclic α‐chloroamides, primarily those incorporating pharmacological pyrazolone cores, as potent synthons for synthesizing valuable spirocyclic γ‐lactam architectures. This protocol exhibits 52–96% yields, impressive substrate compatibility, and scale‐up capacity. Importantly, this study also represents one of the rare examples that harness enaminone C−N bond cleavage to engineer relevant spirocyclic γ‐lactam skeletons of biological interest. Moreover, we propose a plausible mechanistic explanation to elucidate the outstanding chemical outcomes observed, thereby enriching the synthetic toolbox for pyrazolone chemistry and α‐haloamide‐mediated reactions.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202301175</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-0832-1864</orcidid><orcidid>https://orcid.org/0000-0003-3200-4682</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1615-4150 |
ispartof | Advanced synthesis & catalysis, 2024-01, Vol.366 (2), p.269-276 |
issn | 1615-4150 1615-4169 |
language | eng |
recordid | cdi_proquest_journals_2919910857 |
source | Wiley Online Library Journals Frontfile Complete |
subjects | Amides Cycloaddition Enaminone Pyrazolone Pyrazolones Spirocyclic Architecture Substrates α-Haloamide γ-Lactam |
title | [3+2] Cycloaddition of Rationally Designed Trisubstituted Cyclic α‐Chloroamide: an Alternative Strategy for Accessing Spirocyclic γ‐Lactam Architecture |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-21T17%3A51%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=%5B3+2%5D%20Cycloaddition%20of%20Rationally%20Designed%20Trisubstituted%20Cyclic%20%CE%B1%E2%80%90Chloroamide:%20an%20Alternative%20Strategy%20for%20Accessing%20Spirocyclic%20%CE%B3%E2%80%90Lactam%20Architecture&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Li,%20Yang&rft.date=2024-01-30&rft.volume=366&rft.issue=2&rft.spage=269&rft.epage=276&rft.pages=269-276&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.202301175&rft_dat=%3Cproquest_cross%3E2919910857%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=2919910857&rft_id=info:pmid/&rfr_iscdi=true |