Synthesis of Rigid Analogues of Flavone by Intramolecular Heck Reaction

Synthesis of Rigid Analogues of Flavone by Intramolecular Heck Reaction

A novel concise method to synthesize rigid analogues of flavone by an intramolecular Heck reaction with wide substrate scope was developed. The key intermediates 3‐(2‐bromobenzyl)‐4H‐chromen‐4‐ones were prepared easily in two steps. Most compounds were obtained with moderate to good yields (34–90 %...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:European journal of organic chemistry 2015-05, Vol.2015 (14), p.3040-3043
Hauptverfasser: Hou, Chuanwei, Chen, Hao, Xu, Xing, Zhu, Fangxia, Guo, Lei, Jiang, Min, Yang, Chunhao, Deng, Lianfu
Format: Artikel
Sprache:eng
Schlagworte:
Cross-coupling
Flavone
Heck reaction
Palladium
Synthetic methods
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 3043
container_issue 14
container_start_page 3040
container_title European journal of organic chemistry
container_volume 2015
creator Hou, Chuanwei
Chen, Hao
Xu, Xing
Zhu, Fangxia
Guo, Lei
Jiang, Min
Yang, Chunhao
Deng, Lianfu
description A novel concise method to synthesize rigid analogues of flavone by an intramolecular Heck reaction with wide substrate scope was developed. The key intermediates 3‐(2‐bromobenzyl)‐4H‐chromen‐4‐ones were prepared easily in two steps. Most compounds were obtained with moderate to good yields (34–90 % yield, 19 examples). As the title reaction shows, rigid analogues of flavone were synthesized by an intramolecular Heck reaction from 3‐(2‐bromobenzyl)‐4H‐chromen‐4‐ones, which could be prepared easily in two steps. Most compounds were obtained with moderate to good yields.
doi_str_mv 10.1002/ejoc.201500180
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1678448234</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3674047841</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4950-aa7f6ddffaef53bff930e9d1d6b8d99a0fa8653ea5599a48119627a19adf5d3b3</originalsourceid><addsrcrecordid>eNqFkEtPwzAQhCMEEqVw5RyJc8o6jh37WKq-UEWlAqI3y43tkjaNi50C-fekBCFunHZ3NN9qNEFwjaCHAOJbvbFZLwZEABCDk6CDgPMIKIfTZk9wEiGOl-fBhfcbAOCUok4wfqzL6lX73IfWhIt8nauwX8rCrg_6WxoV8t2WOlzV4bSsnNzZQmeHQrpworNtuNAyq3JbXgZnRhZeX_3MbvA8Gj4NJtFsPp4O-rMoSziBSMrUUKWMkdoQvDKGY9BcIUVXTHEuwUhGCdaSkOZKGEKcxqlEXCpDFF7hbnDT_t07-9ZErMTGHlwT2AtEU5YkLMZJ4-q1rsxZ7502Yu_ynXS1QCCOZYljWeK3rAbgLfCRF7r-xy2G9_PBXzZq2dxX-vOXlW4raIpTIl4exoItYszullgw_AWJV30t</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1678448234</pqid></control><display><type>article</type><title>Synthesis of Rigid Analogues of Flavone by Intramolecular Heck Reaction</title><source>Access via Wiley Online Library</source><creator>Hou, Chuanwei ; Chen, Hao ; Xu, Xing ; Zhu, Fangxia ; Guo, Lei ; Jiang, Min ; Yang, Chunhao ; Deng, Lianfu</creator><creatorcontrib>Hou, Chuanwei ; Chen, Hao ; Xu, Xing ; Zhu, Fangxia ; Guo, Lei ; Jiang, Min ; Yang, Chunhao ; Deng, Lianfu</creatorcontrib><description>A novel concise method to synthesize rigid analogues of flavone by an intramolecular Heck reaction with wide substrate scope was developed. The key intermediates 3‐(2‐bromobenzyl)‐4H‐chromen‐4‐ones were prepared easily in two steps. Most compounds were obtained with moderate to good yields (34–90 % yield, 19 examples). As the title reaction shows, rigid analogues of flavone were synthesized by an intramolecular Heck reaction from 3‐(2‐bromobenzyl)‐4H‐chromen‐4‐ones, which could be prepared easily in two steps. Most compounds were obtained with moderate to good yields.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201500180</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Cross-coupling ; Flavone ; Heck reaction ; Palladium ; Synthetic methods</subject><ispartof>European journal of organic chemistry, 2015-05, Vol.2015 (14), p.3040-3043</ispartof><rights>Copyright © 2015 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><rights>Copyright © 2015 WILEY-VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4950-aa7f6ddffaef53bff930e9d1d6b8d99a0fa8653ea5599a48119627a19adf5d3b3</citedby><cites>FETCH-LOGICAL-c4950-aa7f6ddffaef53bff930e9d1d6b8d99a0fa8653ea5599a48119627a19adf5d3b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201500180$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201500180$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Hou, Chuanwei</creatorcontrib><creatorcontrib>Chen, Hao</creatorcontrib><creatorcontrib>Xu, Xing</creatorcontrib><creatorcontrib>Zhu, Fangxia</creatorcontrib><creatorcontrib>Guo, Lei</creatorcontrib><creatorcontrib>Jiang, Min</creatorcontrib><creatorcontrib>Yang, Chunhao</creatorcontrib><creatorcontrib>Deng, Lianfu</creatorcontrib><title>Synthesis of Rigid Analogues of Flavone by Intramolecular Heck Reaction</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>A novel concise method to synthesize rigid analogues of flavone by an intramolecular Heck reaction with wide substrate scope was developed. The key intermediates 3‐(2‐bromobenzyl)‐4H‐chromen‐4‐ones were prepared easily in two steps. Most compounds were obtained with moderate to good yields (34–90 % yield, 19 examples). As the title reaction shows, rigid analogues of flavone were synthesized by an intramolecular Heck reaction from 3‐(2‐bromobenzyl)‐4H‐chromen‐4‐ones, which could be prepared easily in two steps. Most compounds were obtained with moderate to good yields.</description><subject>Cross-coupling</subject><subject>Flavone</subject><subject>Heck reaction</subject><subject>Palladium</subject><subject>Synthetic methods</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkEtPwzAQhCMEEqVw5RyJc8o6jh37WKq-UEWlAqI3y43tkjaNi50C-fekBCFunHZ3NN9qNEFwjaCHAOJbvbFZLwZEABCDk6CDgPMIKIfTZk9wEiGOl-fBhfcbAOCUok4wfqzL6lX73IfWhIt8nauwX8rCrg_6WxoV8t2WOlzV4bSsnNzZQmeHQrpworNtuNAyq3JbXgZnRhZeX_3MbvA8Gj4NJtFsPp4O-rMoSziBSMrUUKWMkdoQvDKGY9BcIUVXTHEuwUhGCdaSkOZKGEKcxqlEXCpDFF7hbnDT_t07-9ZErMTGHlwT2AtEU5YkLMZJ4-q1rsxZ7502Yu_ynXS1QCCOZYljWeK3rAbgLfCRF7r-xy2G9_PBXzZq2dxX-vOXlW4raIpTIl4exoItYszullgw_AWJV30t</recordid><startdate>201505</startdate><enddate>201505</enddate><creator>Hou, Chuanwei</creator><creator>Chen, Hao</creator><creator>Xu, Xing</creator><creator>Zhu, Fangxia</creator><creator>Guo, Lei</creator><creator>Jiang, Min</creator><creator>Yang, Chunhao</creator><creator>Deng, Lianfu</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201505</creationdate><title>Synthesis of Rigid Analogues of Flavone by Intramolecular Heck Reaction</title><author>Hou, Chuanwei ; Chen, Hao ; Xu, Xing ; Zhu, Fangxia ; Guo, Lei ; Jiang, Min ; Yang, Chunhao ; Deng, Lianfu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4950-aa7f6ddffaef53bff930e9d1d6b8d99a0fa8653ea5599a48119627a19adf5d3b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Cross-coupling</topic><topic>Flavone</topic><topic>Heck reaction</topic><topic>Palladium</topic><topic>Synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hou, Chuanwei</creatorcontrib><creatorcontrib>Chen, Hao</creatorcontrib><creatorcontrib>Xu, Xing</creatorcontrib><creatorcontrib>Zhu, Fangxia</creatorcontrib><creatorcontrib>Guo, Lei</creatorcontrib><creatorcontrib>Jiang, Min</creatorcontrib><creatorcontrib>Yang, Chunhao</creatorcontrib><creatorcontrib>Deng, Lianfu</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hou, Chuanwei</au><au>Chen, Hao</au><au>Xu, Xing</au><au>Zhu, Fangxia</au><au>Guo, Lei</au><au>Jiang, Min</au><au>Yang, Chunhao</au><au>Deng, Lianfu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Rigid Analogues of Flavone by Intramolecular Heck Reaction</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2015-05</date><risdate>2015</risdate><volume>2015</volume><issue>14</issue><spage>3040</spage><epage>3043</epage><pages>3040-3043</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A novel concise method to synthesize rigid analogues of flavone by an intramolecular Heck reaction with wide substrate scope was developed. The key intermediates 3‐(2‐bromobenzyl)‐4H‐chromen‐4‐ones were prepared easily in two steps. Most compounds were obtained with moderate to good yields (34–90 % yield, 19 examples). As the title reaction shows, rigid analogues of flavone were synthesized by an intramolecular Heck reaction from 3‐(2‐bromobenzyl)‐4H‐chromen‐4‐ones, which could be prepared easily in two steps. Most compounds were obtained with moderate to good yields.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201500180</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1434-193X
ispartof European journal of organic chemistry, 2015-05, Vol.2015 (14), p.3040-3043
issn 1434-193X
1099-0690
language eng
recordid cdi_proquest_journals_1678448234
source Access via Wiley Online Library
subjects Cross-coupling
Flavone
Heck reaction
Palladium
Synthetic methods
title Synthesis of Rigid Analogues of Flavone by Intramolecular Heck Reaction
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T04%3A39%3A03IST&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=Synthesis%20of%20Rigid%20Analogues%20of%20Flavone%20by%20Intramolecular%20Heck%20Reaction&rft.jtitle=European%20journal%20of%20organic%20chemistry&rft.au=Hou,%20Chuanwei&rft.date=2015-05&rft.volume=2015&rft.issue=14&rft.spage=3040&rft.epage=3043&rft.pages=3040-3043&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002/ejoc.201500180&rft_dat=%3Cproquest_cross%3E3674047841%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=1678448234&rft_id=info:pmid/&rfr_iscdi=true