One‐Pot Sequential Bromination and Fluorination to Access 3‐Fluoroimidazo[1,2‐a]pyridines from Arylketones
3‐Fluoro‐2‐arylimidazo[1,2‐a]pyridines were selectively synthesised in one‐pot from acetophenones and 2‐aminopyridines under mild conditions. The sequence of reactions involved bromination, condensation, and late‐stage fluorination. Two halogenating reagents play key roles in the process. We found t...
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| Veröffentlicht in: | European journal of organic chemistry 2018-07, Vol.2018 (26), p.3432-3436 |
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| container_title | European journal of organic chemistry |
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| creator | Udavant, Rohini N. Yadav, Ashok R. Shinde, Sandip S. |
| description | 3‐Fluoro‐2‐arylimidazo[1,2‐a]pyridines were selectively synthesised in one‐pot from acetophenones and 2‐aminopyridines under mild conditions. The sequence of reactions involved bromination, condensation, and late‐stage fluorination. Two halogenating reagents play key roles in the process. We found that tetrabutylammonium tribromide and SelectfluorTM gave excellent yields of the desired products in the one‐pot sequential reaction.
3‐Fluoro‐2‐arylimidazo[1,2‐a]pyridines were synthesised in one‐pot from acetophenones and 2‐aminopyridines under mild conditions. The reaction sequence involves bromination, condensation, and fluorination steps. The halogenating reagents TBATB (tetrabutylammonium tribromide), and SelectfluorTM play key roles without interfering with the other steps. |
| doi_str_mv | 10.1002/ejoc.201800578 |
| format | Article |
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3‐Fluoro‐2‐arylimidazo[1,2‐a]pyridines were synthesised in one‐pot from acetophenones and 2‐aminopyridines under mild conditions. The reaction sequence involves bromination, condensation, and fluorination steps. The halogenating reagents TBATB (tetrabutylammonium tribromide), and SelectfluorTM play key roles without interfering with the other steps.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201800578</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Bromination ; Bromine ; Condensates ; Cyclization ; Fluorination ; Fluorine ; Fused‐ring systems ; Halogenation ; Nitrogen heterocycles ; Pyridines ; Reagents</subject><ispartof>European journal of organic chemistry, 2018-07, Vol.2018 (26), p.3432-3436</ispartof><rights>2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3178-4b80c28593392285f33b199f15cb8c14f1151b7e91e5eef036388a1026a7ebcb3</citedby><cites>FETCH-LOGICAL-c3178-4b80c28593392285f33b199f15cb8c14f1151b7e91e5eef036388a1026a7ebcb3</cites><orcidid>0000-0002-1320-565X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201800578$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201800578$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Udavant, Rohini N.</creatorcontrib><creatorcontrib>Yadav, Ashok R.</creatorcontrib><creatorcontrib>Shinde, Sandip S.</creatorcontrib><title>One‐Pot Sequential Bromination and Fluorination to Access 3‐Fluoroimidazo[1,2‐a]pyridines from Arylketones</title><title>European journal of organic chemistry</title><description>3‐Fluoro‐2‐arylimidazo[1,2‐a]pyridines were selectively synthesised in one‐pot from acetophenones and 2‐aminopyridines under mild conditions. The sequence of reactions involved bromination, condensation, and late‐stage fluorination. Two halogenating reagents play key roles in the process. We found that tetrabutylammonium tribromide and SelectfluorTM gave excellent yields of the desired products in the one‐pot sequential reaction.
3‐Fluoro‐2‐arylimidazo[1,2‐a]pyridines were synthesised in one‐pot from acetophenones and 2‐aminopyridines under mild conditions. The reaction sequence involves bromination, condensation, and fluorination steps. The halogenating reagents TBATB (tetrabutylammonium tribromide), and SelectfluorTM play key roles without interfering with the other steps.</description><subject>Bromination</subject><subject>Bromine</subject><subject>Condensates</subject><subject>Cyclization</subject><subject>Fluorination</subject><subject>Fluorine</subject><subject>Fused‐ring systems</subject><subject>Halogenation</subject><subject>Nitrogen heterocycles</subject><subject>Pyridines</subject><subject>Reagents</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFUMtKAzEUHUTBWt26Drh16r2TeSTLWqwPChVUEERCJs1A6nRSkykyrvwEv9EvMbU-lq7O5dxzzuWeKDpEGCBAcqLnVg0SQAaQFWwr6iFwHkPOYTvMKU1j5PR-N9rzfg4APM-xFy2njf54e7-2LbnRzyvdtEbW5NTZhWlka2xDZDMj43pl3Q_RWjJUSntPaHB-raxZmJl8tQ94nAROPi47Z2am0Z5UIYoMXVc_6dYGYj_aqWTt9cE39qO78dnt6CKeTM8vR8NJrCgWLE5LBiphGaeUJwErSkvkvMJMlUxhWiFmWBaao860roDmlDGJkOSy0KUqaT862uQunQ1_-VbM7co14aRIoAAoaI55UA02KuWs905XYunMQrpOIIh1q2LdqvhtNRj4xvBiat39oxZnV9PRn_cTaxt_Ug</recordid><startdate>20180713</startdate><enddate>20180713</enddate><creator>Udavant, Rohini N.</creator><creator>Yadav, Ashok R.</creator><creator>Shinde, Sandip S.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-1320-565X</orcidid></search><sort><creationdate>20180713</creationdate><title>One‐Pot Sequential Bromination and Fluorination to Access 3‐Fluoroimidazo[1,2‐a]pyridines from Arylketones</title><author>Udavant, Rohini N. ; Yadav, Ashok R. ; Shinde, Sandip S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3178-4b80c28593392285f33b199f15cb8c14f1151b7e91e5eef036388a1026a7ebcb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Bromination</topic><topic>Bromine</topic><topic>Condensates</topic><topic>Cyclization</topic><topic>Fluorination</topic><topic>Fluorine</topic><topic>Fused‐ring systems</topic><topic>Halogenation</topic><topic>Nitrogen heterocycles</topic><topic>Pyridines</topic><topic>Reagents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Udavant, Rohini N.</creatorcontrib><creatorcontrib>Yadav, Ashok R.</creatorcontrib><creatorcontrib>Shinde, Sandip S.</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Udavant, Rohini N.</au><au>Yadav, Ashok R.</au><au>Shinde, Sandip S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One‐Pot Sequential Bromination and Fluorination to Access 3‐Fluoroimidazo[1,2‐a]pyridines from Arylketones</atitle><jtitle>European journal of organic chemistry</jtitle><date>2018-07-13</date><risdate>2018</risdate><volume>2018</volume><issue>26</issue><spage>3432</spage><epage>3436</epage><pages>3432-3436</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>3‐Fluoro‐2‐arylimidazo[1,2‐a]pyridines were selectively synthesised in one‐pot from acetophenones and 2‐aminopyridines under mild conditions. The sequence of reactions involved bromination, condensation, and late‐stage fluorination. Two halogenating reagents play key roles in the process. We found that tetrabutylammonium tribromide and SelectfluorTM gave excellent yields of the desired products in the one‐pot sequential reaction.
3‐Fluoro‐2‐arylimidazo[1,2‐a]pyridines were synthesised in one‐pot from acetophenones and 2‐aminopyridines under mild conditions. The reaction sequence involves bromination, condensation, and fluorination steps. The halogenating reagents TBATB (tetrabutylammonium tribromide), and SelectfluorTM play key roles without interfering with the other steps.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201800578</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-1320-565X</orcidid></addata></record> |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Bromination Bromine Condensates Cyclization Fluorination Fluorine Fused‐ring systems Halogenation Nitrogen heterocycles Pyridines Reagents |
| title | One‐Pot Sequential Bromination and Fluorination to Access 3‐Fluoroimidazo[1,2‐a]pyridines from Arylketones |
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