Efficient Method for the Synthesis of Hetarenoindanones Based on 3-Arylhetarenes and Their Conversion into Hetarenoindenes

A series of hetarenoindanones have been prepared by direct double metalation of the appropriate 3-phenylhetarene with butyllithium in the presence of TMEDA followed by treatment of the resulting dilithium compound with ethyl N,N-dimethylcarbamate. All hetarenoindanones were reduced according to Wolf...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2004-08, Vol.69 (16), p.5476-5479
Hauptverfasser: Kashulin, Igor A, Nifant'ev, Ilya E
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 5479
container_issue 16
container_start_page 5476
container_title Journal of organic chemistry
container_volume 69
creator Kashulin, Igor A
Nifant'ev, Ilya E
description A series of hetarenoindanones have been prepared by direct double metalation of the appropriate 3-phenylhetarene with butyllithium in the presence of TMEDA followed by treatment of the resulting dilithium compound with ethyl N,N-dimethylcarbamate. All hetarenoindanones were reduced according to Wolff−Kishner by hydrazine in the presence of ΚOH to the corresponding hetarenoindenes.
doi_str_mv 10.1021/jo049504w
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_66764076</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>66764076</sourcerecordid><originalsourceid>FETCH-LOGICAL-a349t-6f1e5532818af99d56299e968f96a15f29239f865212eb99676df4143d52b5c63</originalsourceid><addsrcrecordid>eNpt0MtOGzEUBmALFUFIWfQFKm-KxGLAl7FnvKQREASoXIKQurGcmWPFNLGpPWkJT4-jiWgXeHMW5_N_pB-hL5QcUcLo8VMgpRKk_LuFBlQwUkhFyk9oQAhjBWeS76K9lJ5IfkKIHbSbUV3VhA7Q66m1rnHgO3wN3Sy02IaIuxng-5XPI7mEg8Vj6EwEH5xvjQ8eEv5uErQ4eMyLk7iaz3qQF8a3eDIDF_Eo-D8Qk8vI-S78H7KWn9G2NfME-5s5RA9np5PRuLj6cX4xOrkqDC9VV0hLQQjOalobq1QrJFMKlKytkoYKyxTjytZSMMpgqpSsZGtLWvJWsKloJB-igz73OYbfS0idXrjUwHxuPIRl0jL_KEm1hoc9bGJIKYLVz9EtTFxpSvS6aP1edLZfN6HL6QLaf3LTbAZFD1zq4OV9b-IvLSteCT25udfy5-P57eXdrb7J_lvvTZPynWX0uZMPDr8B7FCUng</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>66764076</pqid></control><display><type>article</type><title>Efficient Method for the Synthesis of Hetarenoindanones Based on 3-Arylhetarenes and Their Conversion into Hetarenoindenes</title><source>American Chemical Society Journals</source><creator>Kashulin, Igor A ; Nifant'ev, Ilya E</creator><creatorcontrib>Kashulin, Igor A ; Nifant'ev, Ilya E</creatorcontrib><description>A series of hetarenoindanones have been prepared by direct double metalation of the appropriate 3-phenylhetarene with butyllithium in the presence of TMEDA followed by treatment of the resulting dilithium compound with ethyl N,N-dimethylcarbamate. All hetarenoindanones were reduced according to Wolff−Kishner by hydrazine in the presence of ΚOH to the corresponding hetarenoindenes.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo049504w</identifier><identifier>PMID: 15287801</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2004-08, Vol.69 (16), p.5476-5479</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>Copyright 2004 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a349t-6f1e5532818af99d56299e968f96a15f29239f865212eb99676df4143d52b5c63</citedby><cites>FETCH-LOGICAL-a349t-6f1e5532818af99d56299e968f96a15f29239f865212eb99676df4143d52b5c63</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/jo049504w$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo049504w$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15287801$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kashulin, Igor A</creatorcontrib><creatorcontrib>Nifant'ev, Ilya E</creatorcontrib><title>Efficient Method for the Synthesis of Hetarenoindanones Based on 3-Arylhetarenes and Their Conversion into Hetarenoindenes</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A series of hetarenoindanones have been prepared by direct double metalation of the appropriate 3-phenylhetarene with butyllithium in the presence of TMEDA followed by treatment of the resulting dilithium compound with ethyl N,N-dimethylcarbamate. All hetarenoindanones were reduced according to Wolff−Kishner by hydrazine in the presence of ΚOH to the corresponding hetarenoindenes.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNpt0MtOGzEUBmALFUFIWfQFKm-KxGLAl7FnvKQREASoXIKQurGcmWPFNLGpPWkJT4-jiWgXeHMW5_N_pB-hL5QcUcLo8VMgpRKk_LuFBlQwUkhFyk9oQAhjBWeS76K9lJ5IfkKIHbSbUV3VhA7Q66m1rnHgO3wN3Sy02IaIuxng-5XPI7mEg8Vj6EwEH5xvjQ8eEv5uErQ4eMyLk7iaz3qQF8a3eDIDF_Eo-D8Qk8vI-S78H7KWn9G2NfME-5s5RA9np5PRuLj6cX4xOrkqDC9VV0hLQQjOalobq1QrJFMKlKytkoYKyxTjytZSMMpgqpSsZGtLWvJWsKloJB-igz73OYbfS0idXrjUwHxuPIRl0jL_KEm1hoc9bGJIKYLVz9EtTFxpSvS6aP1edLZfN6HL6QLaf3LTbAZFD1zq4OV9b-IvLSteCT25udfy5-P57eXdrb7J_lvvTZPynWX0uZMPDr8B7FCUng</recordid><startdate>20040806</startdate><enddate>20040806</enddate><creator>Kashulin, Igor A</creator><creator>Nifant'ev, Ilya E</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20040806</creationdate><title>Efficient Method for the Synthesis of Hetarenoindanones Based on 3-Arylhetarenes and Their Conversion into Hetarenoindenes</title><author>Kashulin, Igor A ; Nifant'ev, Ilya E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a349t-6f1e5532818af99d56299e968f96a15f29239f865212eb99676df4143d52b5c63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kashulin, Igor A</creatorcontrib><creatorcontrib>Nifant'ev, Ilya E</creatorcontrib><collection>Istex</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>Kashulin, Igor A</au><au>Nifant'ev, Ilya E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient Method for the Synthesis of Hetarenoindanones Based on 3-Arylhetarenes and Their Conversion into Hetarenoindenes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2004-08-06</date><risdate>2004</risdate><volume>69</volume><issue>16</issue><spage>5476</spage><epage>5479</epage><pages>5476-5479</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A series of hetarenoindanones have been prepared by direct double metalation of the appropriate 3-phenylhetarene with butyllithium in the presence of TMEDA followed by treatment of the resulting dilithium compound with ethyl N,N-dimethylcarbamate. All hetarenoindanones were reduced according to Wolff−Kishner by hydrazine in the presence of ΚOH to the corresponding hetarenoindenes.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>15287801</pmid><doi>10.1021/jo049504w</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2004-08, Vol.69 (16), p.5476-5479
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_66764076
source American Chemical Society Journals
title Efficient Method for the Synthesis of Hetarenoindanones Based on 3-Arylhetarenes and Their Conversion into Hetarenoindenes
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-19T00%3A22%3A20IST&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%20Method%20for%20the%20Synthesis%20of%20Hetarenoindanones%20Based%20on%203-Arylhetarenes%20and%20Their%20Conversion%20into%20Hetarenoindenes&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Kashulin,%20Igor%20A&rft.date=2004-08-06&rft.volume=69&rft.issue=16&rft.spage=5476&rft.epage=5479&rft.pages=5476-5479&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/jo049504w&rft_dat=%3Cproquest_cross%3E66764076%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=66764076&rft_id=info:pmid/15287801&rfr_iscdi=true