Organic Brønsted acid‐catalyzed cycloadditions of o‐quinone methides with 1, 3‐dicarbonlys: Facile access to xanthenones and chromanones

The in‐situ generation of o‐quinone methides and their inverse‐electron‐demand Diels–Alder reaction in the presence of pentacarboxycyclopentadiene—an organic Brønsted acid—has been reported. The synthesis of xanthenones and chromanones in good to excellent yields from the [4 + 2] cycloaddition of qu...

Full description

Saved in:
Bibliographic Details
Published in:Journal of heterocyclic chemistry 2021-10, Vol.58 (10), p.1971-1982
Main Authors: Thoppe Sivakumar, Priyadarshini, Puthiyaparambath, Sharathna, Suresh Varma, Sanjay, Parameswaran, Sasikumar, Kokkuvayil Vasu, Radhakrishnan
Format: Article
Language:English
Subjects:
Cycloaddition
Diels-Alder reactions
Quinones
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-c2273-76ea8c6c4f44686115ebdb24a17d0b131f9d6a4b33c0a84b76041d8d92d265d43
cites cdi_FETCH-LOGICAL-c2273-76ea8c6c4f44686115ebdb24a17d0b131f9d6a4b33c0a84b76041d8d92d265d43
container_end_page 1982
container_issue 10
container_start_page 1971
container_title Journal of heterocyclic chemistry
container_volume 58
creator Thoppe Sivakumar, Priyadarshini
Puthiyaparambath, Sharathna
Suresh Varma, Sanjay
Parameswaran, Sasikumar
Kokkuvayil Vasu, Radhakrishnan
description The in‐situ generation of o‐quinone methides and their inverse‐electron‐demand Diels–Alder reaction in the presence of pentacarboxycyclopentadiene—an organic Brønsted acid—has been reported. The synthesis of xanthenones and chromanones in good to excellent yields from the [4 + 2] cycloaddition of quinone methides with 1, 3‐dicarbonyls and Meldrum's acid has been accomplished. The development of this method helps in generating a number of biologically potent heterocycles with medicinal applications.
doi_str_mv 10.1002/jhet.4323
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2578648203</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2578648203</sourcerecordid><originalsourceid>FETCH-LOGICAL-c2273-76ea8c6c4f44686115ebdb24a17d0b131f9d6a4b33c0a84b76041d8d92d265d43</originalsourceid><addsrcrecordid>eNp1kD1OAzEQhS0EEiFQcANLVEhssv7Zn9BBlBBQJJog0a28tpd1tLET21FYKm4Ax6HnJpwEJ6GlGs28b95oHgDnKO6hOMb9eS19jxJMDkAHDSiJEjQgh6ATNByhBD8fgxPn5qFFJMs64OPRvjCtOLy131_aeSkg40r8vH9y5lnTvoUBb3ljmBDKK6MdNBU0QV-tlTZawoX0tRLSwY3yNURXkARRKM5saXTTums4Do6NDL5cOge9ga9M-1putx1kOhyorVmwXX8KjirWOHn2V7vgaTyaDSfR9PHufngzjTjGGYmyVLKcp5xWlKZ5ilAiS1FiylAm4hIRVA1EymhJCI9ZTsssjSkSuRhggdNEUNIFF3vfpTWrtXS-mJu11eFkgZMsT2mOYxKoyz3FrXHOyqpYWrVgti1QXGzzLrZ5F9u8A9vfs5vwbPs_WDxMRrPdxi_x_4fd</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2578648203</pqid></control><display><type>article</type><title>Organic Brønsted acid‐catalyzed cycloadditions of o‐quinone methides with 1, 3‐dicarbonlys: Facile access to xanthenones and chromanones</title><source>Wiley-Blackwell Read &amp; Publish Collection</source><creator>Thoppe Sivakumar, Priyadarshini ; Puthiyaparambath, Sharathna ; Suresh Varma, Sanjay ; Parameswaran, Sasikumar ; Kokkuvayil Vasu, Radhakrishnan</creator><creatorcontrib>Thoppe Sivakumar, Priyadarshini ; Puthiyaparambath, Sharathna ; Suresh Varma, Sanjay ; Parameswaran, Sasikumar ; Kokkuvayil Vasu, Radhakrishnan</creatorcontrib><description>The in‐situ generation of o‐quinone methides and their inverse‐electron‐demand Diels–Alder reaction in the presence of pentacarboxycyclopentadiene—an organic Brønsted acid—has been reported. The synthesis of xanthenones and chromanones in good to excellent yields from the [4 + 2] cycloaddition of quinone methides with 1, 3‐dicarbonyls and Meldrum's acid has been accomplished. The development of this method helps in generating a number of biologically potent heterocycles with medicinal applications.</description><identifier>ISSN: 0022-152X</identifier><identifier>EISSN: 1943-5193</identifier><identifier>DOI: 10.1002/jhet.4323</identifier><language>eng</language><publisher>Chichester, UK: John Wiley &amp; Sons, Inc</publisher><subject>Cycloaddition ; Diels-Alder reactions ; Quinones</subject><ispartof>Journal of heterocyclic chemistry, 2021-10, Vol.58 (10), p.1971-1982</ispartof><rights>2021 Wiley Periodicals LLC.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2273-76ea8c6c4f44686115ebdb24a17d0b131f9d6a4b33c0a84b76041d8d92d265d43</citedby><cites>FETCH-LOGICAL-c2273-76ea8c6c4f44686115ebdb24a17d0b131f9d6a4b33c0a84b76041d8d92d265d43</cites><orcidid>0000-0001-8909-3175</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Thoppe Sivakumar, Priyadarshini</creatorcontrib><creatorcontrib>Puthiyaparambath, Sharathna</creatorcontrib><creatorcontrib>Suresh Varma, Sanjay</creatorcontrib><creatorcontrib>Parameswaran, Sasikumar</creatorcontrib><creatorcontrib>Kokkuvayil Vasu, Radhakrishnan</creatorcontrib><title>Organic Brønsted acid‐catalyzed cycloadditions of o‐quinone methides with 1, 3‐dicarbonlys: Facile access to xanthenones and chromanones</title><title>Journal of heterocyclic chemistry</title><description>The in‐situ generation of o‐quinone methides and their inverse‐electron‐demand Diels–Alder reaction in the presence of pentacarboxycyclopentadiene—an organic Brønsted acid—has been reported. The synthesis of xanthenones and chromanones in good to excellent yields from the [4 + 2] cycloaddition of quinone methides with 1, 3‐dicarbonyls and Meldrum's acid has been accomplished. The development of this method helps in generating a number of biologically potent heterocycles with medicinal applications.</description><subject>Cycloaddition</subject><subject>Diels-Alder reactions</subject><subject>Quinones</subject><issn>0022-152X</issn><issn>1943-5193</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp1kD1OAzEQhS0EEiFQcANLVEhssv7Zn9BBlBBQJJog0a28tpd1tLET21FYKm4Ax6HnJpwEJ6GlGs28b95oHgDnKO6hOMb9eS19jxJMDkAHDSiJEjQgh6ATNByhBD8fgxPn5qFFJMs64OPRvjCtOLy131_aeSkg40r8vH9y5lnTvoUBb3ljmBDKK6MdNBU0QV-tlTZawoX0tRLSwY3yNURXkARRKM5saXTTums4Do6NDL5cOge9ga9M-1putx1kOhyorVmwXX8KjirWOHn2V7vgaTyaDSfR9PHufngzjTjGGYmyVLKcp5xWlKZ5ilAiS1FiylAm4hIRVA1EymhJCI9ZTsssjSkSuRhggdNEUNIFF3vfpTWrtXS-mJu11eFkgZMsT2mOYxKoyz3FrXHOyqpYWrVgti1QXGzzLrZ5F9u8A9vfs5vwbPs_WDxMRrPdxi_x_4fd</recordid><startdate>202110</startdate><enddate>202110</enddate><creator>Thoppe Sivakumar, Priyadarshini</creator><creator>Puthiyaparambath, Sharathna</creator><creator>Suresh Varma, Sanjay</creator><creator>Parameswaran, Sasikumar</creator><creator>Kokkuvayil Vasu, Radhakrishnan</creator><general>John Wiley &amp; Sons, Inc</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-8909-3175</orcidid></search><sort><creationdate>202110</creationdate><title>Organic Brønsted acid‐catalyzed cycloadditions of o‐quinone methides with 1, 3‐dicarbonlys: Facile access to xanthenones and chromanones</title><author>Thoppe Sivakumar, Priyadarshini ; Puthiyaparambath, Sharathna ; Suresh Varma, Sanjay ; Parameswaran, Sasikumar ; Kokkuvayil Vasu, Radhakrishnan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2273-76ea8c6c4f44686115ebdb24a17d0b131f9d6a4b33c0a84b76041d8d92d265d43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Cycloaddition</topic><topic>Diels-Alder reactions</topic><topic>Quinones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Thoppe Sivakumar, Priyadarshini</creatorcontrib><creatorcontrib>Puthiyaparambath, Sharathna</creatorcontrib><creatorcontrib>Suresh Varma, Sanjay</creatorcontrib><creatorcontrib>Parameswaran, Sasikumar</creatorcontrib><creatorcontrib>Kokkuvayil Vasu, Radhakrishnan</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of heterocyclic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Thoppe Sivakumar, Priyadarshini</au><au>Puthiyaparambath, Sharathna</au><au>Suresh Varma, Sanjay</au><au>Parameswaran, Sasikumar</au><au>Kokkuvayil Vasu, Radhakrishnan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Organic Brønsted acid‐catalyzed cycloadditions of o‐quinone methides with 1, 3‐dicarbonlys: Facile access to xanthenones and chromanones</atitle><jtitle>Journal of heterocyclic chemistry</jtitle><date>2021-10</date><risdate>2021</risdate><volume>58</volume><issue>10</issue><spage>1971</spage><epage>1982</epage><pages>1971-1982</pages><issn>0022-152X</issn><eissn>1943-5193</eissn><abstract>The in‐situ generation of o‐quinone methides and their inverse‐electron‐demand Diels–Alder reaction in the presence of pentacarboxycyclopentadiene—an organic Brønsted acid—has been reported. The synthesis of xanthenones and chromanones in good to excellent yields from the [4 + 2] cycloaddition of quinone methides with 1, 3‐dicarbonyls and Meldrum's acid has been accomplished. The development of this method helps in generating a number of biologically potent heterocycles with medicinal applications.</abstract><cop>Chichester, UK</cop><pub>John Wiley &amp; Sons, Inc</pub><doi>10.1002/jhet.4323</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0001-8909-3175</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-152X
ispartof Journal of heterocyclic chemistry, 2021-10, Vol.58 (10), p.1971-1982
issn 0022-152X
1943-5193
language eng
recordid cdi_proquest_journals_2578648203
source Wiley-Blackwell Read & Publish Collection
subjects Cycloaddition
Diels-Alder reactions
Quinones
title Organic Brønsted acid‐catalyzed cycloadditions of o‐quinone methides with 1, 3‐dicarbonlys: Facile access to xanthenones and chromanones
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T20%3A54%3A26IST&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=Organic%20Br%C3%B8nsted%20acid%E2%80%90catalyzed%20cycloadditions%20of%20o%E2%80%90quinone%20methides%20with%201,%203%E2%80%90dicarbonlys:%20Facile%20access%20to%20xanthenones%20and%20chromanones&rft.jtitle=Journal%20of%20heterocyclic%20chemistry&rft.au=Thoppe%20Sivakumar,%20Priyadarshini&rft.date=2021-10&rft.volume=58&rft.issue=10&rft.spage=1971&rft.epage=1982&rft.pages=1971-1982&rft.issn=0022-152X&rft.eissn=1943-5193&rft_id=info:doi/10.1002/jhet.4323&rft_dat=%3Cproquest_cross%3E2578648203%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c2273-76ea8c6c4f44686115ebdb24a17d0b131f9d6a4b33c0a84b76041d8d92d265d43%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2578648203&rft_id=info:pmid/&rfr_iscdi=true