Direct Assembly of Benzo[e]indoles by Diels-Alder Reaction of Arynes and 2-Vinylpyrroles

A direct synthetic strategy for the construction of benzo[e]indoles by Diels–Alder reaction of 2‐vinylpyrroles and arynes was developed. By introducing CHPh2 as the N‐protecting group, the arynes selectively reacted with the external vinyl group instead of the pyrrole ring itself. A series of substi...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	European journal of organic chemistry 2016-06, Vol.2016 (17), p.2929-2932
Hauptverfasser:	Yuan, Jing, Wu, Xin-Yan, Sha, Feng
Format:	Artikel
Sprache:	eng
Schlagworte:	Arynes Cycloaddition Fused-ring systems Nitrogen heterocycles Protecting groups
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	2932
container_issue	17
container_start_page	2929
container_title	European journal of organic chemistry
container_volume	2016
creator	Yuan, Jing Wu, Xin-Yan Sha, Feng
description	A direct synthetic strategy for the construction of benzo[e]indoles by Diels–Alder reaction of 2‐vinylpyrroles and arynes was developed. By introducing CHPh2 as the N‐protecting group, the arynes selectively reacted with the external vinyl group instead of the pyrrole ring itself. A series of substituted benzo[e]indoles were afforded with high selectivity in good yields. A direct and efficient strategy for the construction of the benzo[e]indole skeleton is developed by Diels–Alder reaction of arynes and easily accessible 2‐alkenylpyrroles. By introducing CHPh2 as the N‐protecting group, the arynes can selectively react with the external vinyl group instead of the pyrrole ring itself in a step‐ and atom‐economical manner.
doi_str_mv	10.1002/ejoc.201600334
format	Article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1799024625</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>4097745251</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3554-eac15569b8def7cb5a00a798320348cdfae8a0617da02de4d52bda5bb807bbde3</originalsourceid><addsrcrecordid>eNqFkEFLw0AQhYMoWKtXzwHPqbPZbJI9xrS2Sm1BtBZElt3sBFLTpO62aPz1pkSKN0_zDt_3Bp7jXBIYEAD_Gld1NvCBhACUBkdOjwDnHoQcjtsc0MAjnC5PnTNrVwDAw5D0nOWwMJht3cRaXKuycevcvcHqu37Ft6LSdYnWVY07LLC0XlJqNO4jymxb1NUeTUxTtYSstOt7i6Jqyk1jzN46d05yWVq8-L195_l29JROvOl8fJcmUy-jjAVe20UYC7mKNeZRppgEkBGPqQ80iDOdS4wlhCTSEnyNgWa-0pIpFUOklEbad6663o2pP3Zot2JV70zVvhQk4hz8IPRZSw06KjO1tQZzsTHFWppGEBD79cR-PXFYrxV4J3wWJTb_0GJ0P0__ul7nFnaLXwdXmncRRjRi4mU2FunDIp2xeCIo_QE0OIN3</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1799024625</pqid></control><display><type>article</type><title>Direct Assembly of Benzo[e]indoles by Diels-Alder Reaction of Arynes and 2-Vinylpyrroles</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Yuan, Jing ; Wu, Xin-Yan ; Sha, Feng</creator><creatorcontrib>Yuan, Jing ; Wu, Xin-Yan ; Sha, Feng</creatorcontrib><description>A direct synthetic strategy for the construction of benzo[e]indoles by Diels–Alder reaction of 2‐vinylpyrroles and arynes was developed. By introducing CHPh2 as the N‐protecting group, the arynes selectively reacted with the external vinyl group instead of the pyrrole ring itself. A series of substituted benzo[e]indoles were afforded with high selectivity in good yields. A direct and efficient strategy for the construction of the benzo[e]indole skeleton is developed by Diels–Alder reaction of arynes and easily accessible 2‐alkenylpyrroles. By introducing CHPh2 as the N‐protecting group, the arynes can selectively react with the external vinyl group instead of the pyrrole ring itself in a step‐ and atom‐economical manner.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201600334</identifier><language>eng</language><publisher>Weinheim: Blackwell Publishing Ltd</publisher><subject>Arynes ; Cycloaddition ; Fused-ring systems ; Nitrogen heterocycles ; Protecting groups</subject><ispartof>European journal of organic chemistry, 2016-06, Vol.2016 (17), p.2929-2932</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3554-eac15569b8def7cb5a00a798320348cdfae8a0617da02de4d52bda5bb807bbde3</citedby><cites>FETCH-LOGICAL-c3554-eac15569b8def7cb5a00a798320348cdfae8a0617da02de4d52bda5bb807bbde3</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.201600334$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201600334$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27907,27908,45557,45558</link.rule.ids></links><search><creatorcontrib>Yuan, Jing</creatorcontrib><creatorcontrib>Wu, Xin-Yan</creatorcontrib><creatorcontrib>Sha, Feng</creatorcontrib><title>Direct Assembly of Benzo[e]indoles by Diels-Alder Reaction of Arynes and 2-Vinylpyrroles</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>A direct synthetic strategy for the construction of benzo[e]indoles by Diels–Alder reaction of 2‐vinylpyrroles and arynes was developed. By introducing CHPh2 as the N‐protecting group, the arynes selectively reacted with the external vinyl group instead of the pyrrole ring itself. A series of substituted benzo[e]indoles were afforded with high selectivity in good yields. A direct and efficient strategy for the construction of the benzo[e]indole skeleton is developed by Diels–Alder reaction of arynes and easily accessible 2‐alkenylpyrroles. By introducing CHPh2 as the N‐protecting group, the arynes can selectively react with the external vinyl group instead of the pyrrole ring itself in a step‐ and atom‐economical manner.</description><subject>Arynes</subject><subject>Cycloaddition</subject><subject>Fused-ring systems</subject><subject>Nitrogen heterocycles</subject><subject>Protecting groups</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkEFLw0AQhYMoWKtXzwHPqbPZbJI9xrS2Sm1BtBZElt3sBFLTpO62aPz1pkSKN0_zDt_3Bp7jXBIYEAD_Gld1NvCBhACUBkdOjwDnHoQcjtsc0MAjnC5PnTNrVwDAw5D0nOWwMJht3cRaXKuycevcvcHqu37Ft6LSdYnWVY07LLC0XlJqNO4jymxb1NUeTUxTtYSstOt7i6Jqyk1jzN46d05yWVq8-L195_l29JROvOl8fJcmUy-jjAVe20UYC7mKNeZRppgEkBGPqQ80iDOdS4wlhCTSEnyNgWa-0pIpFUOklEbad6663o2pP3Zot2JV70zVvhQk4hz8IPRZSw06KjO1tQZzsTHFWppGEBD79cR-PXFYrxV4J3wWJTb_0GJ0P0__ul7nFnaLXwdXmncRRjRi4mU2FunDIp2xeCIo_QE0OIN3</recordid><startdate>201606</startdate><enddate>201606</enddate><creator>Yuan, Jing</creator><creator>Wu, Xin-Yan</creator><creator>Sha, Feng</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201606</creationdate><title>Direct Assembly of Benzo[e]indoles by Diels-Alder Reaction of Arynes and 2-Vinylpyrroles</title><author>Yuan, Jing ; Wu, Xin-Yan ; Sha, Feng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3554-eac15569b8def7cb5a00a798320348cdfae8a0617da02de4d52bda5bb807bbde3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Arynes</topic><topic>Cycloaddition</topic><topic>Fused-ring systems</topic><topic>Nitrogen heterocycles</topic><topic>Protecting groups</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yuan, Jing</creatorcontrib><creatorcontrib>Wu, Xin-Yan</creatorcontrib><creatorcontrib>Sha, Feng</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>Yuan, Jing</au><au>Wu, Xin-Yan</au><au>Sha, Feng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct Assembly of Benzo[e]indoles by Diels-Alder Reaction of Arynes and 2-Vinylpyrroles</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2016-06</date><risdate>2016</risdate><volume>2016</volume><issue>17</issue><spage>2929</spage><epage>2932</epage><pages>2929-2932</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A direct synthetic strategy for the construction of benzo[e]indoles by Diels–Alder reaction of 2‐vinylpyrroles and arynes was developed. By introducing CHPh2 as the N‐protecting group, the arynes selectively reacted with the external vinyl group instead of the pyrrole ring itself. A series of substituted benzo[e]indoles were afforded with high selectivity in good yields. A direct and efficient strategy for the construction of the benzo[e]indole skeleton is developed by Diels–Alder reaction of arynes and easily accessible 2‐alkenylpyrroles. By introducing CHPh2 as the N‐protecting group, the arynes can selectively react with the external vinyl group instead of the pyrrole ring itself in a step‐ and atom‐economical manner.</abstract><cop>Weinheim</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/ejoc.201600334</doi><tpages>4</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 1434-193X
ispartof	European journal of organic chemistry, 2016-06, Vol.2016 (17), p.2929-2932
issn	1434-193X 1099-0690
language	eng
recordid	cdi_proquest_journals_1799024625
source	Wiley Online Library Journals Frontfile Complete
subjects	Arynes Cycloaddition Fused-ring systems Nitrogen heterocycles Protecting groups
title	Direct Assembly of Benzo[e]indoles by Diels-Alder Reaction of Arynes and 2-Vinylpyrroles
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-17T07%3A07%3A39IST&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=Direct%20Assembly%20of%20Benzo%5Be%5Dindoles%20by%20Diels-Alder%20Reaction%20of%20Arynes%20and%202-Vinylpyrroles&rft.jtitle=European%20journal%20of%20organic%20chemistry&rft.au=Yuan,%20Jing&rft.date=2016-06&rft.volume=2016&rft.issue=17&rft.spage=2929&rft.epage=2932&rft.pages=2929-2932&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002/ejoc.201600334&rft_dat=%3Cproquest_cross%3E4097745251%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=1799024625&rft_id=info:pmid/&rfr_iscdi=true