Sequential alkylation/gold-catalyzed annulation reactions of anilines with propargylic bromide derivatives

Preliminary results of sequential alkylation/gold-catalyzed annulation reactions of anilines with propargylic bromide derivatives to provide quinoline scaffolds are described. The efficiency of NaAuCl 4·2H 2O in the sequential procedure was investigated and compared with different transition metal s...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Tetrahedron letters 2011-10, Vol.52 (40), p.5145-5148
Hauptverfasser: Alfonsi, Maria, Arcadi, Antonio, Chiarini, Marco, Marinelli, Fabio
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 5148
container_issue 40
container_start_page 5145
container_title Tetrahedron letters
container_volume 52
creator Alfonsi, Maria
Arcadi, Antonio
Chiarini, Marco
Marinelli, Fabio
description Preliminary results of sequential alkylation/gold-catalyzed annulation reactions of anilines with propargylic bromide derivatives to provide quinoline scaffolds are described. The efficiency of NaAuCl 4·2H 2O in the sequential procedure was investigated and compared with different transition metal salts and Au(I) complexes. Selectivity of the reaction of aniline derivatives with propargylic bromides has also been investigated.
doi_str_mv 10.1016/j.tetlet.2011.07.115
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1744681224</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040403911012536</els_id><sourcerecordid>1744681224</sourcerecordid><originalsourceid>FETCH-LOGICAL-c369t-b7d52408cf70b0f8fbaf1d83802a065f8f9b80abff89d7ce769d739ec6372f3c3</originalsourceid><addsrcrecordid>eNp9UE1v1DAQtRCVWAr_gEMuSFySjuMkdi5IqKIFqVIP0LM1scfFizdZbO-i5dfXq1QcO5cZvXlvPh5jHzg0HPhwtW0y5UC5aYHzBmTDef-KbbiSoha94q_ZBqCDugMxvmFvU9pCiUHBhm1_0J8DzdljqDD8PgXMfpmvHpdga4MZw-kf2Qrn-bB2qkhozkWqFldwH_xMqfrr869qH5c9xsdT8Kaa4rLzlipL0R-L8kjpHbtwGBK9f86X7OHm68_rb_Xd_e336y93tRHDmOtJ2r7tQBknYQKn3ISOWyUUtAhDX4BxUoCTc2q00pAcShIjmUHI1gkjLtmndW65p_yWst75ZCgEnGk5JM1l1w2Kt21XqN1KNXFJKZLT--h3GE-agz5bq7d6tVafrdUgdbG2yD4-b8BkMLiIs_Hpv7btegApeeF9XnlU3j16ijoZT7Mh6yOZrO3iX170BL74lKU</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1744681224</pqid></control><display><type>article</type><title>Sequential alkylation/gold-catalyzed annulation reactions of anilines with propargylic bromide derivatives</title><source>ScienceDirect Journals (5 years ago - present)</source><creator>Alfonsi, Maria ; Arcadi, Antonio ; Chiarini, Marco ; Marinelli, Fabio</creator><creatorcontrib>Alfonsi, Maria ; Arcadi, Antonio ; Chiarini, Marco ; Marinelli, Fabio</creatorcontrib><description>Preliminary results of sequential alkylation/gold-catalyzed annulation reactions of anilines with propargylic bromide derivatives to provide quinoline scaffolds are described. The efficiency of NaAuCl 4·2H 2O in the sequential procedure was investigated and compared with different transition metal salts and Au(I) complexes. Selectivity of the reaction of aniline derivatives with propargylic bromides has also been investigated.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2011.07.115</identifier><identifier>CODEN: TELEAY</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Alkylation ; Aniline ; Bromides ; Chemical reactions ; Chemistry ; Derivatives ; Exact sciences and technology ; Gold catalysis ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Intramolecular hydroarylation ; N-Propargylation ; Noncondensed benzenic compounds ; Organic chemistry ; Preparations and properties ; Quinoline ; Quinolines ; Sequential reactions ; Transition metals</subject><ispartof>Tetrahedron letters, 2011-10, Vol.52 (40), p.5145-5148</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c369t-b7d52408cf70b0f8fbaf1d83802a065f8f9b80abff89d7ce769d739ec6372f3c3</citedby><cites>FETCH-LOGICAL-c369t-b7d52408cf70b0f8fbaf1d83802a065f8f9b80abff89d7ce769d739ec6372f3c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2011.07.115$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3549,27923,27924,45994</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=24500771$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Alfonsi, Maria</creatorcontrib><creatorcontrib>Arcadi, Antonio</creatorcontrib><creatorcontrib>Chiarini, Marco</creatorcontrib><creatorcontrib>Marinelli, Fabio</creatorcontrib><title>Sequential alkylation/gold-catalyzed annulation reactions of anilines with propargylic bromide derivatives</title><title>Tetrahedron letters</title><description>Preliminary results of sequential alkylation/gold-catalyzed annulation reactions of anilines with propargylic bromide derivatives to provide quinoline scaffolds are described. The efficiency of NaAuCl 4·2H 2O in the sequential procedure was investigated and compared with different transition metal salts and Au(I) complexes. Selectivity of the reaction of aniline derivatives with propargylic bromides has also been investigated.</description><subject>Alkylation</subject><subject>Aniline</subject><subject>Bromides</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Derivatives</subject><subject>Exact sciences and technology</subject><subject>Gold catalysis</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Intramolecular hydroarylation</subject><subject>N-Propargylation</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Quinoline</subject><subject>Quinolines</subject><subject>Sequential reactions</subject><subject>Transition metals</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9UE1v1DAQtRCVWAr_gEMuSFySjuMkdi5IqKIFqVIP0LM1scfFizdZbO-i5dfXq1QcO5cZvXlvPh5jHzg0HPhwtW0y5UC5aYHzBmTDef-KbbiSoha94q_ZBqCDugMxvmFvU9pCiUHBhm1_0J8DzdljqDD8PgXMfpmvHpdga4MZw-kf2Qrn-bB2qkhozkWqFldwH_xMqfrr869qH5c9xsdT8Kaa4rLzlipL0R-L8kjpHbtwGBK9f86X7OHm68_rb_Xd_e336y93tRHDmOtJ2r7tQBknYQKn3ISOWyUUtAhDX4BxUoCTc2q00pAcShIjmUHI1gkjLtmndW65p_yWst75ZCgEnGk5JM1l1w2Kt21XqN1KNXFJKZLT--h3GE-agz5bq7d6tVafrdUgdbG2yD4-b8BkMLiIs_Hpv7btegApeeF9XnlU3j16ijoZT7Mh6yOZrO3iX170BL74lKU</recordid><startdate>20111005</startdate><enddate>20111005</enddate><creator>Alfonsi, Maria</creator><creator>Arcadi, Antonio</creator><creator>Chiarini, Marco</creator><creator>Marinelli, Fabio</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20111005</creationdate><title>Sequential alkylation/gold-catalyzed annulation reactions of anilines with propargylic bromide derivatives</title><author>Alfonsi, Maria ; Arcadi, Antonio ; Chiarini, Marco ; Marinelli, Fabio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c369t-b7d52408cf70b0f8fbaf1d83802a065f8f9b80abff89d7ce769d739ec6372f3c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Alkylation</topic><topic>Aniline</topic><topic>Bromides</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Derivatives</topic><topic>Exact sciences and technology</topic><topic>Gold catalysis</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Intramolecular hydroarylation</topic><topic>N-Propargylation</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Quinoline</topic><topic>Quinolines</topic><topic>Sequential reactions</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Alfonsi, Maria</creatorcontrib><creatorcontrib>Arcadi, Antonio</creatorcontrib><creatorcontrib>Chiarini, Marco</creatorcontrib><creatorcontrib>Marinelli, Fabio</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Alfonsi, Maria</au><au>Arcadi, Antonio</au><au>Chiarini, Marco</au><au>Marinelli, Fabio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sequential alkylation/gold-catalyzed annulation reactions of anilines with propargylic bromide derivatives</atitle><jtitle>Tetrahedron letters</jtitle><date>2011-10-05</date><risdate>2011</risdate><volume>52</volume><issue>40</issue><spage>5145</spage><epage>5148</epage><pages>5145-5148</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><coden>TELEAY</coden><abstract>Preliminary results of sequential alkylation/gold-catalyzed annulation reactions of anilines with propargylic bromide derivatives to provide quinoline scaffolds are described. The efficiency of NaAuCl 4·2H 2O in the sequential procedure was investigated and compared with different transition metal salts and Au(I) complexes. Selectivity of the reaction of aniline derivatives with propargylic bromides has also been investigated.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2011.07.115</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0040-4039
ispartof Tetrahedron letters, 2011-10, Vol.52 (40), p.5145-5148
issn 0040-4039
1873-3581
language eng
recordid cdi_proquest_miscellaneous_1744681224
source ScienceDirect Journals (5 years ago - present)
subjects Alkylation
Aniline
Bromides
Chemical reactions
Chemistry
Derivatives
Exact sciences and technology
Gold catalysis
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Intramolecular hydroarylation
N-Propargylation
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Quinoline
Quinolines
Sequential reactions
Transition metals
title Sequential alkylation/gold-catalyzed annulation reactions of anilines with propargylic bromide derivatives
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-09T00%3A06%3A36IST&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=Sequential%20alkylation/gold-catalyzed%20annulation%20reactions%20of%20anilines%20with%20propargylic%20bromide%20derivatives&rft.jtitle=Tetrahedron%20letters&rft.au=Alfonsi,%20Maria&rft.date=2011-10-05&rft.volume=52&rft.issue=40&rft.spage=5145&rft.epage=5148&rft.pages=5145-5148&rft.issn=0040-4039&rft.eissn=1873-3581&rft.coden=TELEAY&rft_id=info:doi/10.1016/j.tetlet.2011.07.115&rft_dat=%3Cproquest_cross%3E1744681224%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=1744681224&rft_id=info:pmid/&rft_els_id=S0040403911012536&rfr_iscdi=true