Efficient, “Tin-Free” Radical Cyclization to Aromatic Systems. Synthesis of 5,6,8,9,10,11- Hexahydroindolo[2,1-a]isoquinolines

Efficient radical cyclization of alkyl iodides to various aromatic systems including pyrrole, indole, isoquinolone, pyridone, and benzene, mediated by dicumyl peroxide, is described. The methodology was used to provide access to 5,6,8,9,10,11-hexahydroindolo[2,1-a]isoquinoline derivatives.

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2004-05, Vol.69 (11), p.4001-4004
Hauptverfasser: Menes-Arzate, Martha, Martínez, Roberto, Cruz-Almanza, Raymundo, Muchowski, Joseph M, Osornio, Yazmin M, Miranda, Luis D
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 4004
container_issue 11
container_start_page 4001
container_title Journal of organic chemistry
container_volume 69
creator Menes-Arzate, Martha
Martínez, Roberto
Cruz-Almanza, Raymundo
Muchowski, Joseph M
Osornio, Yazmin M
Miranda, Luis D
description Efficient radical cyclization of alkyl iodides to various aromatic systems including pyrrole, indole, isoquinolone, pyridone, and benzene, mediated by dicumyl peroxide, is described. The methodology was used to provide access to 5,6,8,9,10,11-hexahydroindolo[2,1-a]isoquinoline derivatives.
doi_str_mv 10.1021/jo0497048
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_71965386</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>71965386</sourcerecordid><originalsourceid>FETCH-LOGICAL-a379t-44ed1e2cde95e70635613dc5db22aa8aa9bcdda1c4d2f17c0b6c505fc224fad3</originalsourceid><addsrcrecordid>eNptkN1qFDEYhoModq0eeAMyJwrCpOZ3MnNYlm4rFKx2z0TCt0mGps4kbTILXY9Kr6PeXK_EyC6tB-Yk-cjD-708CL2l5IASRj9dRiI6RUT7DM2oZAQ3HRHP0YwQxjBnDd9Dr3K-JOVIKV-iPSqp5ESIGbo76ntvvAtTXT3c3i99wIvk3MPt7-obWG9gqOYbM_hfMPkYqilWhymOZTDV-SZPbswH5RGmC5d9rmJfybqp27qrKakpxdWJu4GLjU3RBxuH-J3VFMMPn-P12oc4-ODya_SihyG7N7t7Hy0XR8v5CT79cvx5fniKgatuwkI4Sx0z1nXSKdJw2VBujbQrxgBagG5lrAVqhGU9VYasGiOJ7A1jogfL99GHbexVKstdnvTos3HDAMHFddaKdo3kbVPAj1vQpJhzcr2-Sn6EtNGU6L--9aPvwr7bha5Xo7NP5E5wAd7vAMhFZp8gGJ__4VTLlSCFw1vOF6k3j_-QfupGcSX18uxcf-XqTB2LheZPuWBy6bNOoaj7T8E_1ECj3Q</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>71965386</pqid></control><display><type>article</type><title>Efficient, “Tin-Free” Radical Cyclization to Aromatic Systems. Synthesis of 5,6,8,9,10,11- Hexahydroindolo[2,1-a]isoquinolines</title><source>American Chemical Society</source><creator>Menes-Arzate, Martha ; Martínez, Roberto ; Cruz-Almanza, Raymundo ; Muchowski, Joseph M ; Osornio, Yazmin M ; Miranda, Luis D</creator><creatorcontrib>Menes-Arzate, Martha ; Martínez, Roberto ; Cruz-Almanza, Raymundo ; Muchowski, Joseph M ; Osornio, Yazmin M ; Miranda, Luis D</creatorcontrib><description>Efficient radical cyclization of alkyl iodides to various aromatic systems including pyrrole, indole, isoquinolone, pyridone, and benzene, mediated by dicumyl peroxide, is described. The methodology was used to provide access to 5,6,8,9,10,11-hexahydroindolo[2,1-a]isoquinoline derivatives.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0497048</identifier><identifier>PMID: 15153044</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2004-05, Vol.69 (11), p.4001-4004</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-44ed1e2cde95e70635613dc5db22aa8aa9bcdda1c4d2f17c0b6c505fc224fad3</citedby><cites>FETCH-LOGICAL-a379t-44ed1e2cde95e70635613dc5db22aa8aa9bcdda1c4d2f17c0b6c505fc224fad3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo0497048$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo0497048$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27074,27922,27923,56736,56786</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=15783740$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15153044$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Menes-Arzate, Martha</creatorcontrib><creatorcontrib>Martínez, Roberto</creatorcontrib><creatorcontrib>Cruz-Almanza, Raymundo</creatorcontrib><creatorcontrib>Muchowski, Joseph M</creatorcontrib><creatorcontrib>Osornio, Yazmin M</creatorcontrib><creatorcontrib>Miranda, Luis D</creatorcontrib><title>Efficient, “Tin-Free” Radical Cyclization to Aromatic Systems. Synthesis of 5,6,8,9,10,11- Hexahydroindolo[2,1-a]isoquinolines</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Efficient radical cyclization of alkyl iodides to various aromatic systems including pyrrole, indole, isoquinolone, pyridone, and benzene, mediated by dicumyl peroxide, is described. The methodology was used to provide access to 5,6,8,9,10,11-hexahydroindolo[2,1-a]isoquinoline derivatives.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNptkN1qFDEYhoModq0eeAMyJwrCpOZ3MnNYlm4rFKx2z0TCt0mGps4kbTILXY9Kr6PeXK_EyC6tB-Yk-cjD-708CL2l5IASRj9dRiI6RUT7DM2oZAQ3HRHP0YwQxjBnDd9Dr3K-JOVIKV-iPSqp5ESIGbo76ntvvAtTXT3c3i99wIvk3MPt7-obWG9gqOYbM_hfMPkYqilWhymOZTDV-SZPbswH5RGmC5d9rmJfybqp27qrKakpxdWJu4GLjU3RBxuH-J3VFMMPn-P12oc4-ODya_SihyG7N7t7Hy0XR8v5CT79cvx5fniKgatuwkI4Sx0z1nXSKdJw2VBujbQrxgBagG5lrAVqhGU9VYasGiOJ7A1jogfL99GHbexVKstdnvTos3HDAMHFddaKdo3kbVPAj1vQpJhzcr2-Sn6EtNGU6L--9aPvwr7bha5Xo7NP5E5wAd7vAMhFZp8gGJ__4VTLlSCFw1vOF6k3j_-QfupGcSX18uxcf-XqTB2LheZPuWBy6bNOoaj7T8E_1ECj3Q</recordid><startdate>20040528</startdate><enddate>20040528</enddate><creator>Menes-Arzate, Martha</creator><creator>Martínez, Roberto</creator><creator>Cruz-Almanza, Raymundo</creator><creator>Muchowski, Joseph M</creator><creator>Osornio, Yazmin M</creator><creator>Miranda, Luis D</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20040528</creationdate><title>Efficient, “Tin-Free” Radical Cyclization to Aromatic Systems. Synthesis of 5,6,8,9,10,11- Hexahydroindolo[2,1-a]isoquinolines</title><author>Menes-Arzate, Martha ; Martínez, Roberto ; Cruz-Almanza, Raymundo ; Muchowski, Joseph M ; Osornio, Yazmin M ; Miranda, Luis D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-44ed1e2cde95e70635613dc5db22aa8aa9bcdda1c4d2f17c0b6c505fc224fad3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Menes-Arzate, Martha</creatorcontrib><creatorcontrib>Martínez, Roberto</creatorcontrib><creatorcontrib>Cruz-Almanza, Raymundo</creatorcontrib><creatorcontrib>Muchowski, Joseph M</creatorcontrib><creatorcontrib>Osornio, Yazmin M</creatorcontrib><creatorcontrib>Miranda, Luis D</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Menes-Arzate, Martha</au><au>Martínez, Roberto</au><au>Cruz-Almanza, Raymundo</au><au>Muchowski, Joseph M</au><au>Osornio, Yazmin M</au><au>Miranda, Luis D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient, “Tin-Free” Radical Cyclization to Aromatic Systems. Synthesis of 5,6,8,9,10,11- Hexahydroindolo[2,1-a]isoquinolines</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2004-05-28</date><risdate>2004</risdate><volume>69</volume><issue>11</issue><spage>4001</spage><epage>4004</epage><pages>4001-4004</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Efficient radical cyclization of alkyl iodides to various aromatic systems including pyrrole, indole, isoquinolone, pyridone, and benzene, mediated by dicumyl peroxide, is described. The methodology was used to provide access to 5,6,8,9,10,11-hexahydroindolo[2,1-a]isoquinoline derivatives.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15153044</pmid><doi>10.1021/jo0497048</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2004-05, Vol.69 (11), p.4001-4004
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_71965386
source American Chemical Society
subjects Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
title Efficient, “Tin-Free” Radical Cyclization to Aromatic Systems. Synthesis of 5,6,8,9,10,11- Hexahydroindolo[2,1-a]isoquinolines
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-14T15%3A31%3A05IST&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=Efficient,%20%E2%80%9CTin-Free%E2%80%9D%20Radical%20Cyclization%20to%20Aromatic%20Systems.%20Synthesis%20of%205,6,8,9,10,11-%20Hexahydroindolo%5B2,1-a%5Disoquinolines&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Menes-Arzate,%20Martha&rft.date=2004-05-28&rft.volume=69&rft.issue=11&rft.spage=4001&rft.epage=4004&rft.pages=4001-4004&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo0497048&rft_dat=%3Cproquest_cross%3E71965386%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=71965386&rft_id=info:pmid/15153044&rfr_iscdi=true