General Entry into o‐,o′‐Heteroatom‐Linked N‐(Hetero)aryl‐Imidazole Motifs by Gold‐Catalysed Formal [3+2]‐Dipolar Cycloaddition

A general redox‐neutral approach into the o‐,o′‐heteroatom‐linked N‐(hetero)aryl‐imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench‐stable N‐(heteroaryl)‐pyridinium‐N‐aminides by formal gold‐c...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-06, Vol.359 (11), p.1837-1843
Main Authors: Garzón, Miguel, Arce, Elsa M., Reddy, Raju Jannapu, Davies, Paul W.
Format: Article
Language:English
Subjects:
Aromatic compounds
Cycloaddition
dipoles
Gold
Imidazole
nitrogen heterocycles
nucleophilic nitrenoids
Scaffolds
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c3949-8869b4d8f69d3577cd74a5777abbf8f560d9deefcaace7d6071f516f8fb64a383
cites cdi_FETCH-LOGICAL-c3949-8869b4d8f69d3577cd74a5777abbf8f560d9deefcaace7d6071f516f8fb64a383
container_end_page 1843
container_issue 11
container_start_page 1837
container_title Advanced synthesis & catalysis
container_volume 359
creator Garzón, Miguel
Arce, Elsa M.
Reddy, Raju Jannapu
Davies, Paul W.
description A general redox‐neutral approach into the o‐,o′‐heteroatom‐linked N‐(hetero)aryl‐imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench‐stable N‐(heteroaryl)‐pyridinium‐N‐aminides by formal gold‐catalysed [3+2]‐dipolar cycloadditions across ynamides. Broad structural variety and functional group tolerance allows rapid access into diverse functionalised scaffolds, as exemplified by the preparation of 8 different heteroaromatic cores.
doi_str_mv 10.1002/adsc.201700249
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1920432409</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1920432409</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3949-8869b4d8f69d3577cd74a5777abbf8f560d9deefcaace7d6071f516f8fb64a383</originalsourceid><addsrcrecordid>eNqFUEtOwzAUjBBIlMKWdSQ2IEix83O8ROlXKrAAVghZTuxILm5c7FQorLgBnIUjcRJeFVSWbDxvNDPvyeN5xxgNMELhJReuHIQIEyAx3fF6OMVJEOOU7m7nBO17B84tENgyQnrex0TW0nLtj-rGtr6qG-Ob7_fPC3i-AKeykdbwxiyBzFX9LIV_A-NpJ5xx22qgs6US_M1o6V-bRlXOL1p_YrQAKecN162D3NjYJVx6jM7DJxCGamU0t37eltpwIVSjTH3o7VVcO3n0i33vYTy6z6fB_HYyy6_mQRnRmAZZltIiFlmVUhElhJSCxByQ8KKosipJkaBCyqrkvJREpIjgKsEpSEUa8yiL-t5Jt3dlzctauoYtzNrWcJJhGqI4CmNEwTXoXKU1zllZsZVVS_gzw4htSmeb0tm2dAjQLvCqtGz_cbOr4V3-l_0BvLiPeg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1920432409</pqid></control><display><type>article</type><title>General Entry into o‐,o′‐Heteroatom‐Linked N‐(Hetero)aryl‐Imidazole Motifs by Gold‐Catalysed Formal [3+2]‐Dipolar Cycloaddition</title><source>Wiley-Blackwell Read &amp; Publish Collection</source><creator>Garzón, Miguel ; Arce, Elsa M. ; Reddy, Raju Jannapu ; Davies, Paul W.</creator><creatorcontrib>Garzón, Miguel ; Arce, Elsa M. ; Reddy, Raju Jannapu ; Davies, Paul W.</creatorcontrib><description>A general redox‐neutral approach into the o‐,o′‐heteroatom‐linked N‐(hetero)aryl‐imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench‐stable N‐(heteroaryl)‐pyridinium‐N‐aminides by formal gold‐catalysed [3+2]‐dipolar cycloadditions across ynamides. Broad structural variety and functional group tolerance allows rapid access into diverse functionalised scaffolds, as exemplified by the preparation of 8 different heteroaromatic cores.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201700249</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Aromatic compounds ; Cycloaddition ; dipoles ; Gold ; Imidazole ; nitrogen heterocycles ; nucleophilic nitrenoids ; Scaffolds</subject><ispartof>Advanced synthesis &amp; catalysis, 2017-06, Vol.359 (11), p.1837-1843</ispartof><rights>2017 Wiley‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3949-8869b4d8f69d3577cd74a5777abbf8f560d9deefcaace7d6071f516f8fb64a383</citedby><cites>FETCH-LOGICAL-c3949-8869b4d8f69d3577cd74a5777abbf8f560d9deefcaace7d6071f516f8fb64a383</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Garzón, Miguel</creatorcontrib><creatorcontrib>Arce, Elsa M.</creatorcontrib><creatorcontrib>Reddy, Raju Jannapu</creatorcontrib><creatorcontrib>Davies, Paul W.</creatorcontrib><title>General Entry into o‐,o′‐Heteroatom‐Linked N‐(Hetero)aryl‐Imidazole Motifs by Gold‐Catalysed Formal [3+2]‐Dipolar Cycloaddition</title><title>Advanced synthesis &amp; catalysis</title><description>A general redox‐neutral approach into the o‐,o′‐heteroatom‐linked N‐(hetero)aryl‐imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench‐stable N‐(heteroaryl)‐pyridinium‐N‐aminides by formal gold‐catalysed [3+2]‐dipolar cycloadditions across ynamides. Broad structural variety and functional group tolerance allows rapid access into diverse functionalised scaffolds, as exemplified by the preparation of 8 different heteroaromatic cores.</description><subject>Aromatic compounds</subject><subject>Cycloaddition</subject><subject>dipoles</subject><subject>Gold</subject><subject>Imidazole</subject><subject>nitrogen heterocycles</subject><subject>nucleophilic nitrenoids</subject><subject>Scaffolds</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFUEtOwzAUjBBIlMKWdSQ2IEix83O8ROlXKrAAVghZTuxILm5c7FQorLgBnIUjcRJeFVSWbDxvNDPvyeN5xxgNMELhJReuHIQIEyAx3fF6OMVJEOOU7m7nBO17B84tENgyQnrex0TW0nLtj-rGtr6qG-Ob7_fPC3i-AKeykdbwxiyBzFX9LIV_A-NpJ5xx22qgs6US_M1o6V-bRlXOL1p_YrQAKecN162D3NjYJVx6jM7DJxCGamU0t37eltpwIVSjTH3o7VVcO3n0i33vYTy6z6fB_HYyy6_mQRnRmAZZltIiFlmVUhElhJSCxByQ8KKosipJkaBCyqrkvJREpIjgKsEpSEUa8yiL-t5Jt3dlzctauoYtzNrWcJJhGqI4CmNEwTXoXKU1zllZsZVVS_gzw4htSmeb0tm2dAjQLvCqtGz_cbOr4V3-l_0BvLiPeg</recordid><startdate>20170606</startdate><enddate>20170606</enddate><creator>Garzón, Miguel</creator><creator>Arce, Elsa M.</creator><creator>Reddy, Raju Jannapu</creator><creator>Davies, Paul W.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20170606</creationdate><title>General Entry into o‐,o′‐Heteroatom‐Linked N‐(Hetero)aryl‐Imidazole Motifs by Gold‐Catalysed Formal [3+2]‐Dipolar Cycloaddition</title><author>Garzón, Miguel ; Arce, Elsa M. ; Reddy, Raju Jannapu ; Davies, Paul W.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3949-8869b4d8f69d3577cd74a5777abbf8f560d9deefcaace7d6071f516f8fb64a383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Aromatic compounds</topic><topic>Cycloaddition</topic><topic>dipoles</topic><topic>Gold</topic><topic>Imidazole</topic><topic>nitrogen heterocycles</topic><topic>nucleophilic nitrenoids</topic><topic>Scaffolds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Garzón, Miguel</creatorcontrib><creatorcontrib>Arce, Elsa M.</creatorcontrib><creatorcontrib>Reddy, Raju Jannapu</creatorcontrib><creatorcontrib>Davies, Paul W.</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis &amp; catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Garzón, Miguel</au><au>Arce, Elsa M.</au><au>Reddy, Raju Jannapu</au><au>Davies, Paul W.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>General Entry into o‐,o′‐Heteroatom‐Linked N‐(Hetero)aryl‐Imidazole Motifs by Gold‐Catalysed Formal [3+2]‐Dipolar Cycloaddition</atitle><jtitle>Advanced synthesis &amp; catalysis</jtitle><date>2017-06-06</date><risdate>2017</risdate><volume>359</volume><issue>11</issue><spage>1837</spage><epage>1843</epage><pages>1837-1843</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A general redox‐neutral approach into the o‐,o′‐heteroatom‐linked N‐(hetero)aryl‐imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench‐stable N‐(heteroaryl)‐pyridinium‐N‐aminides by formal gold‐catalysed [3+2]‐dipolar cycloadditions across ynamides. Broad structural variety and functional group tolerance allows rapid access into diverse functionalised scaffolds, as exemplified by the preparation of 8 different heteroaromatic cores.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201700249</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1615-4150
ispartof Advanced synthesis & catalysis, 2017-06, Vol.359 (11), p.1837-1843
issn 1615-4150
1615-4169
language eng
recordid cdi_proquest_journals_1920432409
source Wiley-Blackwell Read & Publish Collection
subjects Aromatic compounds
Cycloaddition
dipoles
Gold
Imidazole
nitrogen heterocycles
nucleophilic nitrenoids
Scaffolds
title General Entry into o‐,o′‐Heteroatom‐Linked N‐(Hetero)aryl‐Imidazole Motifs by Gold‐Catalysed Formal [3+2]‐Dipolar Cycloaddition
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-23T04%3A49%3A23IST&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=General%20Entry%20into%20o%E2%80%90,o%E2%80%B2%E2%80%90Heteroatom%E2%80%90Linked%20N%E2%80%90(Hetero)aryl%E2%80%90Imidazole%20Motifs%20by%20Gold%E2%80%90Catalysed%20Formal%20%5B3+2%5D%E2%80%90Dipolar%20Cycloaddition&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Garz%C3%B3n,%20Miguel&rft.date=2017-06-06&rft.volume=359&rft.issue=11&rft.spage=1837&rft.epage=1843&rft.pages=1837-1843&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201700249&rft_dat=%3Cproquest_cross%3E1920432409%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c3949-8869b4d8f69d3577cd74a5777abbf8f560d9deefcaace7d6071f516f8fb64a383%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1920432409&rft_id=info:pmid/&rfr_iscdi=true