1,2,3-Triazoles as leaving groups: S N Ar reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles

A new approach was designed for the synthesis of C6-substituted 2-triazolylpurine derivatives. A series of substituted products was obtained in S Ar reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. T...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Beilstein journal of organic chemistry 2021-02, Vol.17, p.410-419
Hauptverfasser: Cīrule, Dace, Novosjolova, Irina, Bizdēna, Ērika, Turks, Māris
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 419
container_issue
container_start_page 410
container_title Beilstein journal of organic chemistry
container_volume 17
creator Cīrule, Dace
Novosjolova, Irina
Bizdēna, Ērika
Turks, Māris
description A new approach was designed for the synthesis of C6-substituted 2-triazolylpurine derivatives. A series of substituted products was obtained in S Ar reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. The developed C-O and C-C bond forming reactions clearly show the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as leaving group.
doi_str_mv 10.3762/bjoc.17.37
format Article
fullrecord <record><control><sourceid>pubmed_cross</sourceid><recordid>TN_cdi_crossref_primary_10_3762_bjoc_17_37</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>33633809</sourcerecordid><originalsourceid>FETCH-LOGICAL-c999-179112842664f7598bfa7c4e0c48368a7647fbc874c35da5a03f3386d944a25d3</originalsourceid><addsrcrecordid>eNpNkE1LAzEYhIMotlYv_gDJWZqabLL58FaKX1Dswd6XbDZpU7abJela6q93S1U8vTPwzMA7ANwSPKGCZw_lJpgJEb05A0MiOUY5VeL8nx6Aq5Q2GDPMMb8EA0o5pRKrIfBknI0pWkavv0JtE9QJ1lZ_-mYFVzF0bXqEH_AdTiOMVpudD02CwcFszFHp0-6UO9RtF33Tx_d-t4YLBHVTwRlqOlPb0K5933wNLpyuk735uSOwfH5azl7RfPHyNpvOkVFKISIUIZlkGefMiVzJ0mlhmMWGScqlFpwJVxopmKF5pXONqetf4ZViTGd5RUfg_lRrYkgpWle00W91PBQEF8e5iuNcBRG96eG7E9x25dZWf-jvPvQbAWVkdQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>1,2,3-Triazoles as leaving groups: S N Ar reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles</title><source>DOAJ Directory of Open Access Journals</source><source>PubMed Central Open Access</source><source>EZB-FREE-00999 freely available EZB journals</source><source>PubMed Central</source><creator>Cīrule, Dace ; Novosjolova, Irina ; Bizdēna, Ērika ; Turks, Māris</creator><creatorcontrib>Cīrule, Dace ; Novosjolova, Irina ; Bizdēna, Ērika ; Turks, Māris</creatorcontrib><description>A new approach was designed for the synthesis of C6-substituted 2-triazolylpurine derivatives. A series of substituted products was obtained in S Ar reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. The developed C-O and C-C bond forming reactions clearly show the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as leaving group.</description><identifier>ISSN: 1860-5397</identifier><identifier>EISSN: 1860-5397</identifier><identifier>DOI: 10.3762/bjoc.17.37</identifier><identifier>PMID: 33633809</identifier><language>eng</language><publisher>Germany</publisher><ispartof>Beilstein journal of organic chemistry, 2021-02, Vol.17, p.410-419</ispartof><rights>Copyright © 2021, Cīrule et al.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c999-179112842664f7598bfa7c4e0c48368a7647fbc874c35da5a03f3386d944a25d3</citedby><cites>FETCH-LOGICAL-c999-179112842664f7598bfa7c4e0c48368a7647fbc874c35da5a03f3386d944a25d3</cites><orcidid>0000-0001-5227-0369 ; 0000-0002-8183-1302 ; 0000-0002-9607-2222</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,860,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33633809$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Cīrule, Dace</creatorcontrib><creatorcontrib>Novosjolova, Irina</creatorcontrib><creatorcontrib>Bizdēna, Ērika</creatorcontrib><creatorcontrib>Turks, Māris</creatorcontrib><title>1,2,3-Triazoles as leaving groups: S N Ar reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles</title><title>Beilstein journal of organic chemistry</title><addtitle>Beilstein J Org Chem</addtitle><description>A new approach was designed for the synthesis of C6-substituted 2-triazolylpurine derivatives. A series of substituted products was obtained in S Ar reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. The developed C-O and C-C bond forming reactions clearly show the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as leaving group.</description><issn>1860-5397</issn><issn>1860-5397</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpNkE1LAzEYhIMotlYv_gDJWZqabLL58FaKX1Dswd6XbDZpU7abJela6q93S1U8vTPwzMA7ANwSPKGCZw_lJpgJEb05A0MiOUY5VeL8nx6Aq5Q2GDPMMb8EA0o5pRKrIfBknI0pWkavv0JtE9QJ1lZ_-mYFVzF0bXqEH_AdTiOMVpudD02CwcFszFHp0-6UO9RtF33Tx_d-t4YLBHVTwRlqOlPb0K5933wNLpyuk735uSOwfH5azl7RfPHyNpvOkVFKISIUIZlkGefMiVzJ0mlhmMWGScqlFpwJVxopmKF5pXONqetf4ZViTGd5RUfg_lRrYkgpWle00W91PBQEF8e5iuNcBRG96eG7E9x25dZWf-jvPvQbAWVkdQ</recordid><startdate>20210211</startdate><enddate>20210211</enddate><creator>Cīrule, Dace</creator><creator>Novosjolova, Irina</creator><creator>Bizdēna, Ērika</creator><creator>Turks, Māris</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-5227-0369</orcidid><orcidid>https://orcid.org/0000-0002-8183-1302</orcidid><orcidid>https://orcid.org/0000-0002-9607-2222</orcidid></search><sort><creationdate>20210211</creationdate><title>1,2,3-Triazoles as leaving groups: S N Ar reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles</title><author>Cīrule, Dace ; Novosjolova, Irina ; Bizdēna, Ērika ; Turks, Māris</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c999-179112842664f7598bfa7c4e0c48368a7647fbc874c35da5a03f3386d944a25d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cīrule, Dace</creatorcontrib><creatorcontrib>Novosjolova, Irina</creatorcontrib><creatorcontrib>Bizdēna, Ērika</creatorcontrib><creatorcontrib>Turks, Māris</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Beilstein journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cīrule, Dace</au><au>Novosjolova, Irina</au><au>Bizdēna, Ērika</au><au>Turks, Māris</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>1,2,3-Triazoles as leaving groups: S N Ar reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles</atitle><jtitle>Beilstein journal of organic chemistry</jtitle><addtitle>Beilstein J Org Chem</addtitle><date>2021-02-11</date><risdate>2021</risdate><volume>17</volume><spage>410</spage><epage>419</epage><pages>410-419</pages><issn>1860-5397</issn><eissn>1860-5397</eissn><abstract>A new approach was designed for the synthesis of C6-substituted 2-triazolylpurine derivatives. A series of substituted products was obtained in S Ar reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. The developed C-O and C-C bond forming reactions clearly show the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as leaving group.</abstract><cop>Germany</cop><pmid>33633809</pmid><doi>10.3762/bjoc.17.37</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-5227-0369</orcidid><orcidid>https://orcid.org/0000-0002-8183-1302</orcidid><orcidid>https://orcid.org/0000-0002-9607-2222</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1860-5397
ispartof Beilstein journal of organic chemistry, 2021-02, Vol.17, p.410-419
issn 1860-5397
1860-5397
language eng
recordid cdi_crossref_primary_10_3762_bjoc_17_37
source DOAJ Directory of Open Access Journals; PubMed Central Open Access; EZB-FREE-00999 freely available EZB journals; PubMed Central
title 1,2,3-Triazoles as leaving groups: S N Ar reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-24T06%3A33%3A51IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-pubmed_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=1,2,3-Triazoles%20as%20leaving%20groups:%20S%20N%20Ar%20reactions%20of%202,6-bistriazolylpurines%20with%20O-%20and%20C-nucleophiles&rft.jtitle=Beilstein%20journal%20of%20organic%20chemistry&rft.au=C%C4%ABrule,%20Dace&rft.date=2021-02-11&rft.volume=17&rft.spage=410&rft.epage=419&rft.pages=410-419&rft.issn=1860-5397&rft.eissn=1860-5397&rft_id=info:doi/10.3762/bjoc.17.37&rft_dat=%3Cpubmed_cross%3E33633809%3C/pubmed_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/33633809&rfr_iscdi=true