Transition‐Metal‐Free Regioselective Construction of Diverse 3‐Carbonyl Functionalized 4‐Pyrones via Thermal Wolff‐Rearrangement of Diazodicarbonyls
An efficient protocol for the construction of 3‐carbonyl functionalized 4‐pyrones has been developed using a transition‐metal free thermal cascade reaction of diazodicarbonyls with β‐enamino esters or β‐enamino ketones. This reaction proceeds via cascade carbene generation, ketene formation via ther...
Gespeichert in:
| Veröffentlicht in: | Advanced synthesis & catalysis 2018-12, Vol.360 (23), p.4523-4532 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 4532 |
|---|---|
| container_issue | 23 |
| container_start_page | 4523 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 360 |
| creator | Park, Ga Eul Maezono, Shizuka Mei Bautista Ha, Ji Hyeon Shim, Jae‐Jin Kim, Sung Hong Lee, Yong Rok |
| description | An efficient protocol for the construction of 3‐carbonyl functionalized 4‐pyrones has been developed using a transition‐metal free thermal cascade reaction of diazodicarbonyls with β‐enamino esters or β‐enamino ketones. This reaction proceeds
via
cascade carbene generation, ketene formation
via
thermal Wolff‐rearrangement, nucleophilic addition, intramolecular cyclization, and elimination. This protocol provides a rapid synthetic route to diverse 2,3,5‐trisubstituted 4‐pyrone derivatives.
magnified image |
| doi_str_mv | 10.1002/adsc.201800874 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2140827353</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2140827353</sourcerecordid><originalsourceid>FETCH-LOGICAL-c304t-a1f61393f23f86a4be965a31d14ab2beccb1c0604591cd2dca01b7d919f8f2613</originalsourceid><addsrcrecordid>eNo9kU1OwzAQhS0EEqWwZW2JdYondv6WKFBAKgJVRSwjxxmXVGlc7KRSu-IInIDDcRJcirqa0bxv3mj0CLkENgLGwmtZOTUKGaSMpYk4IgOIIQoExNnxoY_YKTlzbsEYJGmSDMj3zMrW1V1t2p_PryfsZOPr2CLSKc5r47BB1dVrpLlpXWd7tUOp0fTWD61Dyj2fS1uadtPQcd_-AbKpt1hR4bWXjTUtOrquJZ29o13Khr6ZRmuvTVFaf3-OS2y7vancmqpW_37unJxo2Ti8-K9D8jq-m-UPweT5_jG_mQSKM9EFEnQMPOM65DqNpSgxiyPJoQIhy7BEpUpQLGYiykBVYaUkgzKpMsh0qkO_OiRXe9-VNR89uq5YmN76N1wRgmBpmPCIe2q0p5Q1zlnUxcrWS2k3BbBil0Gxy6A4ZMB_AU1BgxM</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2140827353</pqid></control><display><type>article</type><title>Transition‐Metal‐Free Regioselective Construction of Diverse 3‐Carbonyl Functionalized 4‐Pyrones via Thermal Wolff‐Rearrangement of Diazodicarbonyls</title><source>Access via Wiley Online Library</source><creator>Park, Ga Eul ; Maezono, Shizuka Mei Bautista ; Ha, Ji Hyeon ; Shim, Jae‐Jin ; Kim, Sung Hong ; Lee, Yong Rok</creator><creatorcontrib>Park, Ga Eul ; Maezono, Shizuka Mei Bautista ; Ha, Ji Hyeon ; Shim, Jae‐Jin ; Kim, Sung Hong ; Lee, Yong Rok</creatorcontrib><description>An efficient protocol for the construction of 3‐carbonyl functionalized 4‐pyrones has been developed using a transition‐metal free thermal cascade reaction of diazodicarbonyls with β‐enamino esters or β‐enamino ketones. This reaction proceeds
via
cascade carbene generation, ketene formation
via
thermal Wolff‐rearrangement, nucleophilic addition, intramolecular cyclization, and elimination. This protocol provides a rapid synthetic route to diverse 2,3,5‐trisubstituted 4‐pyrone derivatives.
magnified image</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201800874</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Carbonyls ; Cascade chemical reactions ; Esters ; Ketones</subject><ispartof>Advanced synthesis & catalysis, 2018-12, Vol.360 (23), p.4523-4532</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c304t-a1f61393f23f86a4be965a31d14ab2beccb1c0604591cd2dca01b7d919f8f2613</citedby><cites>FETCH-LOGICAL-c304t-a1f61393f23f86a4be965a31d14ab2beccb1c0604591cd2dca01b7d919f8f2613</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Park, Ga Eul</creatorcontrib><creatorcontrib>Maezono, Shizuka Mei Bautista</creatorcontrib><creatorcontrib>Ha, Ji Hyeon</creatorcontrib><creatorcontrib>Shim, Jae‐Jin</creatorcontrib><creatorcontrib>Kim, Sung Hong</creatorcontrib><creatorcontrib>Lee, Yong Rok</creatorcontrib><title>Transition‐Metal‐Free Regioselective Construction of Diverse 3‐Carbonyl Functionalized 4‐Pyrones via Thermal Wolff‐Rearrangement of Diazodicarbonyls</title><title>Advanced synthesis & catalysis</title><description>An efficient protocol for the construction of 3‐carbonyl functionalized 4‐pyrones has been developed using a transition‐metal free thermal cascade reaction of diazodicarbonyls with β‐enamino esters or β‐enamino ketones. This reaction proceeds
via
cascade carbene generation, ketene formation
via
thermal Wolff‐rearrangement, nucleophilic addition, intramolecular cyclization, and elimination. This protocol provides a rapid synthetic route to diverse 2,3,5‐trisubstituted 4‐pyrone derivatives.
magnified image</description><subject>Carbonyls</subject><subject>Cascade chemical reactions</subject><subject>Esters</subject><subject>Ketones</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNo9kU1OwzAQhS0EEqWwZW2JdYondv6WKFBAKgJVRSwjxxmXVGlc7KRSu-IInIDDcRJcirqa0bxv3mj0CLkENgLGwmtZOTUKGaSMpYk4IgOIIQoExNnxoY_YKTlzbsEYJGmSDMj3zMrW1V1t2p_PryfsZOPr2CLSKc5r47BB1dVrpLlpXWd7tUOp0fTWD61Dyj2fS1uadtPQcd_-AbKpt1hR4bWXjTUtOrquJZ29o13Khr6ZRmuvTVFaf3-OS2y7vancmqpW_37unJxo2Ti8-K9D8jq-m-UPweT5_jG_mQSKM9EFEnQMPOM65DqNpSgxiyPJoQIhy7BEpUpQLGYiykBVYaUkgzKpMsh0qkO_OiRXe9-VNR89uq5YmN76N1wRgmBpmPCIe2q0p5Q1zlnUxcrWS2k3BbBil0Gxy6A4ZMB_AU1BgxM</recordid><startdate>20181203</startdate><enddate>20181203</enddate><creator>Park, Ga Eul</creator><creator>Maezono, Shizuka Mei Bautista</creator><creator>Ha, Ji Hyeon</creator><creator>Shim, Jae‐Jin</creator><creator>Kim, Sung Hong</creator><creator>Lee, Yong Rok</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20181203</creationdate><title>Transition‐Metal‐Free Regioselective Construction of Diverse 3‐Carbonyl Functionalized 4‐Pyrones via Thermal Wolff‐Rearrangement of Diazodicarbonyls</title><author>Park, Ga Eul ; Maezono, Shizuka Mei Bautista ; Ha, Ji Hyeon ; Shim, Jae‐Jin ; Kim, Sung Hong ; Lee, Yong Rok</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c304t-a1f61393f23f86a4be965a31d14ab2beccb1c0604591cd2dca01b7d919f8f2613</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Carbonyls</topic><topic>Cascade chemical reactions</topic><topic>Esters</topic><topic>Ketones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Park, Ga Eul</creatorcontrib><creatorcontrib>Maezono, Shizuka Mei Bautista</creatorcontrib><creatorcontrib>Ha, Ji Hyeon</creatorcontrib><creatorcontrib>Shim, Jae‐Jin</creatorcontrib><creatorcontrib>Kim, Sung Hong</creatorcontrib><creatorcontrib>Lee, Yong Rok</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>Park, Ga Eul</au><au>Maezono, Shizuka Mei Bautista</au><au>Ha, Ji Hyeon</au><au>Shim, Jae‐Jin</au><au>Kim, Sung Hong</au><au>Lee, Yong Rok</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Transition‐Metal‐Free Regioselective Construction of Diverse 3‐Carbonyl Functionalized 4‐Pyrones via Thermal Wolff‐Rearrangement of Diazodicarbonyls</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2018-12-03</date><risdate>2018</risdate><volume>360</volume><issue>23</issue><spage>4523</spage><epage>4532</epage><pages>4523-4532</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>An efficient protocol for the construction of 3‐carbonyl functionalized 4‐pyrones has been developed using a transition‐metal free thermal cascade reaction of diazodicarbonyls with β‐enamino esters or β‐enamino ketones. This reaction proceeds
via
cascade carbene generation, ketene formation
via
thermal Wolff‐rearrangement, nucleophilic addition, intramolecular cyclization, and elimination. This protocol provides a rapid synthetic route to diverse 2,3,5‐trisubstituted 4‐pyrone derivatives.
magnified image</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201800874</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2018-12, Vol.360 (23), p.4523-4532 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_proquest_journals_2140827353 |
| source | Access via Wiley Online Library |
| subjects | Carbonyls Cascade chemical reactions Esters Ketones |
| title | Transition‐Metal‐Free Regioselective Construction of Diverse 3‐Carbonyl Functionalized 4‐Pyrones via Thermal Wolff‐Rearrangement of Diazodicarbonyls |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T12%3A07%3A20IST&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=Transition%E2%80%90Metal%E2%80%90Free%20Regioselective%20Construction%20of%20Diverse%203%E2%80%90Carbonyl%20Functionalized%204%E2%80%90Pyrones%20via%20Thermal%20Wolff%E2%80%90Rearrangement%20of%20Diazodicarbonyls&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Park,%20Ga%20Eul&rft.date=2018-12-03&rft.volume=360&rft.issue=23&rft.spage=4523&rft.epage=4532&rft.pages=4523-4532&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201800874&rft_dat=%3Cproquest_cross%3E2140827353%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=2140827353&rft_id=info:pmid/&rfr_iscdi=true |