Bismuth(III)-Catalyzed 1,8-Addition/Cyclization/Rearrangement of Propargylic para-Quinone Methides with 2‑Vinylphenol: Synthesis of Indeno[2,1‑c]chromenes

The unique reactivity of in situ generated propargylic para-quinone methides as a new type of five-carbon synthon has been discovered by a novel bismuth­(III)-catalyzed tandem annulation reaction. This 1,8-addition/cyclization/rearrangement cyclization cascade reaction is characterized by unusual st...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2023-03, Vol.25 (8), p.1299-1304
Main Authors: Zhu, Zhi-Qiang, Wu, Teng-Fei, Pan, Han-Peng, Peng, Jin-Bao, Ma, Ai-Jun, Zhang, Xiang-Zhi
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a345t-874427250fcb02333846ded547eab5b987d0f980afb7a3184e2a1498d9f1b9103
cites cdi_FETCH-LOGICAL-a345t-874427250fcb02333846ded547eab5b987d0f980afb7a3184e2a1498d9f1b9103
container_end_page 1304
container_issue 8
container_start_page 1299
container_title Organic letters
container_volume 25
creator Zhu, Zhi-Qiang
Wu, Teng-Fei
Pan, Han-Peng
Peng, Jin-Bao
Ma, Ai-Jun
Zhang, Xiang-Zhi
description The unique reactivity of in situ generated propargylic para-quinone methides as a new type of five-carbon synthon has been discovered by a novel bismuth­(III)-catalyzed tandem annulation reaction. This 1,8-addition/cyclization/rearrangement cyclization cascade reaction is characterized by unusual structural reconstruction of 2-vinylphenol, involving cleavage of the C1′C2′ bond and formation of four new bonds. This method provides a convenient and mild approach to generate synthetically important functionalized indeno­[2,1-c]­chromenes. The mechanism of the reaction is proposed from several control experiments.
doi_str_mv 10.1021/acs.orglett.3c00179
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2778972723</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2778972723</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-874427250fcb02333846ded547eab5b987d0f980afb7a3184e2a1498d9f1b9103</originalsourceid><addsrcrecordid>eNp9kc1u1DAUhSMEoqXwBEgoyyI1M_5Jxja7dkQhUhH_bBCKHPtm4iqxB9tRla54BV6Ah-NJ8DBDl6zu0dV3ztXVybKnGC0wIngpVVg4vxkgxgVVCGEm7mXHuCK0YKgi9-_0Ch1lj0K4TkjaiIfZEV1xxIVAx9mvCxPGKfandV0_L9YyymG-BZ3jM16ca22icXa5ntVgbuVf_QGk99JuYAQbc9fl77zbSr-ZB6PyJGTxfjLWWcjfQOyNhpDfmNjn5PePn1-MnYdtD9YNL_KPs409BBN2IbXVafuVnOGEqW-q9y7lQ3icPejkEODJYZ5kny9fflq_Lq7evqrX51eFpGUVC87KkjBSoU61iFBKebnSoKuSgWyrVnCmUSc4kl3LJMW8BCJxKbgWHW4FRvQkO93nbr37PkGIzWiCgmGQFtwUGsIYFyydoAmle1R5F4KHrtl6M0o_Nxg1u2KaVExzKKY5FJNczw4HpnYEfef510QClntg5752k7fp3_9G_gFGLqBe</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2778972723</pqid></control><display><type>article</type><title>Bismuth(III)-Catalyzed 1,8-Addition/Cyclization/Rearrangement of Propargylic para-Quinone Methides with 2‑Vinylphenol: Synthesis of Indeno[2,1‑c]chromenes</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Zhu, Zhi-Qiang ; Wu, Teng-Fei ; Pan, Han-Peng ; Peng, Jin-Bao ; Ma, Ai-Jun ; Zhang, Xiang-Zhi</creator><creatorcontrib>Zhu, Zhi-Qiang ; Wu, Teng-Fei ; Pan, Han-Peng ; Peng, Jin-Bao ; Ma, Ai-Jun ; Zhang, Xiang-Zhi</creatorcontrib><description>The unique reactivity of in situ generated propargylic para-quinone methides as a new type of five-carbon synthon has been discovered by a novel bismuth­(III)-catalyzed tandem annulation reaction. This 1,8-addition/cyclization/rearrangement cyclization cascade reaction is characterized by unusual structural reconstruction of 2-vinylphenol, involving cleavage of the C1′C2′ bond and formation of four new bonds. This method provides a convenient and mild approach to generate synthetically important functionalized indeno­[2,1-c]­chromenes. The mechanism of the reaction is proposed from several control experiments.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.3c00179</identifier><identifier>PMID: 36808990</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2023-03, Vol.25 (8), p.1299-1304</ispartof><rights>2023 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-874427250fcb02333846ded547eab5b987d0f980afb7a3184e2a1498d9f1b9103</citedby><cites>FETCH-LOGICAL-a345t-874427250fcb02333846ded547eab5b987d0f980afb7a3184e2a1498d9f1b9103</cites><orcidid>0000-0002-0568-7740 ; 0000-0001-7757-0800 ; 0000-0003-0631-0758</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36808990$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhu, Zhi-Qiang</creatorcontrib><creatorcontrib>Wu, Teng-Fei</creatorcontrib><creatorcontrib>Pan, Han-Peng</creatorcontrib><creatorcontrib>Peng, Jin-Bao</creatorcontrib><creatorcontrib>Ma, Ai-Jun</creatorcontrib><creatorcontrib>Zhang, Xiang-Zhi</creatorcontrib><title>Bismuth(III)-Catalyzed 1,8-Addition/Cyclization/Rearrangement of Propargylic para-Quinone Methides with 2‑Vinylphenol: Synthesis of Indeno[2,1‑c]chromenes</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The unique reactivity of in situ generated propargylic para-quinone methides as a new type of five-carbon synthon has been discovered by a novel bismuth­(III)-catalyzed tandem annulation reaction. This 1,8-addition/cyclization/rearrangement cyclization cascade reaction is characterized by unusual structural reconstruction of 2-vinylphenol, involving cleavage of the C1′C2′ bond and formation of four new bonds. This method provides a convenient and mild approach to generate synthetically important functionalized indeno­[2,1-c]­chromenes. The mechanism of the reaction is proposed from several control experiments.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kc1u1DAUhSMEoqXwBEgoyyI1M_5Jxja7dkQhUhH_bBCKHPtm4iqxB9tRla54BV6Ah-NJ8DBDl6zu0dV3ztXVybKnGC0wIngpVVg4vxkgxgVVCGEm7mXHuCK0YKgi9-_0Ch1lj0K4TkjaiIfZEV1xxIVAx9mvCxPGKfandV0_L9YyymG-BZ3jM16ca22icXa5ntVgbuVf_QGk99JuYAQbc9fl77zbSr-ZB6PyJGTxfjLWWcjfQOyNhpDfmNjn5PePn1-MnYdtD9YNL_KPs409BBN2IbXVafuVnOGEqW-q9y7lQ3icPejkEODJYZ5kny9fflq_Lq7evqrX51eFpGUVC87KkjBSoU61iFBKebnSoKuSgWyrVnCmUSc4kl3LJMW8BCJxKbgWHW4FRvQkO93nbr37PkGIzWiCgmGQFtwUGsIYFyydoAmle1R5F4KHrtl6M0o_Nxg1u2KaVExzKKY5FJNczw4HpnYEfef510QClntg5752k7fp3_9G_gFGLqBe</recordid><startdate>20230303</startdate><enddate>20230303</enddate><creator>Zhu, Zhi-Qiang</creator><creator>Wu, Teng-Fei</creator><creator>Pan, Han-Peng</creator><creator>Peng, Jin-Bao</creator><creator>Ma, Ai-Jun</creator><creator>Zhang, Xiang-Zhi</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-0568-7740</orcidid><orcidid>https://orcid.org/0000-0001-7757-0800</orcidid><orcidid>https://orcid.org/0000-0003-0631-0758</orcidid></search><sort><creationdate>20230303</creationdate><title>Bismuth(III)-Catalyzed 1,8-Addition/Cyclization/Rearrangement of Propargylic para-Quinone Methides with 2‑Vinylphenol: Synthesis of Indeno[2,1‑c]chromenes</title><author>Zhu, Zhi-Qiang ; Wu, Teng-Fei ; Pan, Han-Peng ; Peng, Jin-Bao ; Ma, Ai-Jun ; Zhang, Xiang-Zhi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-874427250fcb02333846ded547eab5b987d0f980afb7a3184e2a1498d9f1b9103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhu, Zhi-Qiang</creatorcontrib><creatorcontrib>Wu, Teng-Fei</creatorcontrib><creatorcontrib>Pan, Han-Peng</creatorcontrib><creatorcontrib>Peng, Jin-Bao</creatorcontrib><creatorcontrib>Ma, Ai-Jun</creatorcontrib><creatorcontrib>Zhang, Xiang-Zhi</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>Zhu, Zhi-Qiang</au><au>Wu, Teng-Fei</au><au>Pan, Han-Peng</au><au>Peng, Jin-Bao</au><au>Ma, Ai-Jun</au><au>Zhang, Xiang-Zhi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bismuth(III)-Catalyzed 1,8-Addition/Cyclization/Rearrangement of Propargylic para-Quinone Methides with 2‑Vinylphenol: Synthesis of Indeno[2,1‑c]chromenes</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2023-03-03</date><risdate>2023</risdate><volume>25</volume><issue>8</issue><spage>1299</spage><epage>1304</epage><pages>1299-1304</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The unique reactivity of in situ generated propargylic para-quinone methides as a new type of five-carbon synthon has been discovered by a novel bismuth­(III)-catalyzed tandem annulation reaction. This 1,8-addition/cyclization/rearrangement cyclization cascade reaction is characterized by unusual structural reconstruction of 2-vinylphenol, involving cleavage of the C1′C2′ bond and formation of four new bonds. This method provides a convenient and mild approach to generate synthetically important functionalized indeno­[2,1-c]­chromenes. The mechanism of the reaction is proposed from several control experiments.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>36808990</pmid><doi>10.1021/acs.orglett.3c00179</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-0568-7740</orcidid><orcidid>https://orcid.org/0000-0001-7757-0800</orcidid><orcidid>https://orcid.org/0000-0003-0631-0758</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2023-03, Vol.25 (8), p.1299-1304
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2778972723
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Bismuth(III)-Catalyzed 1,8-Addition/Cyclization/Rearrangement of Propargylic para-Quinone Methides with 2‑Vinylphenol: Synthesis of Indeno[2,1‑c]chromenes
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T14%3A01%3A34IST&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=Bismuth(III)-Catalyzed%201,8-Addition/Cyclization/Rearrangement%20of%20Propargylic%20para-Quinone%20Methides%20with%202%E2%80%91Vinylphenol:%20Synthesis%20of%20Indeno%5B2,1%E2%80%91c%5Dchromenes&rft.jtitle=Organic%20letters&rft.au=Zhu,%20Zhi-Qiang&rft.date=2023-03-03&rft.volume=25&rft.issue=8&rft.spage=1299&rft.epage=1304&rft.pages=1299-1304&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.3c00179&rft_dat=%3Cproquest_cross%3E2778972723%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a345t-874427250fcb02333846ded547eab5b987d0f980afb7a3184e2a1498d9f1b9103%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2778972723&rft_id=info:pmid/36808990&rfr_iscdi=true