Regioselective Functionalization of 3-Hydroxy-pyridine Carboxylates by Neighboring Group Assistance
Regioselective hydrolysis, transesterification, and aminolysis of unactivated, highly substituted pyridine esters were realized under mild conditions by employing neighboring group assisted catalysis. Excellent yields were achieved without active removal of the alcohol byproduct. Regioselective amin...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2016-10, Vol.11 (20), p.2859-2862 |
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| container_title | Chemistry, an Asian journal |
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| creator | Wojtas, K. Philip Lu, Jin-Yong Krahn, Daniel Arndt, Hans-Dieter |
| description | Regioselective hydrolysis, transesterification, and aminolysis of unactivated, highly substituted pyridine esters were realized under mild conditions by employing neighboring group assisted catalysis. Excellent yields were achieved without active removal of the alcohol byproduct. Regioselective aminolysis had a considerable substrate scope ([hetero]aryl, alkyl and amino acid). A mechanism involving assistance by the deprotonated phenolic OH‐group is suggested for hydrolysis and transesterification.
An unexpected docking site. Free phenolic hydroxy groups in pyridine rings were found to assist the regioselective transformation of proximal ester groups. Selective hydrolysis, transesterification, and amide bond formation can such be realized at very mild pH (8.5) even in the presence of water. |
| doi_str_mv | 10.1002/asia.201601111 |
| format | Article |
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An unexpected docking site. Free phenolic hydroxy groups in pyridine rings were found to assist the regioselective transformation of proximal ester groups. Selective hydrolysis, transesterification, and amide bond formation can such be realized at very mild pH (8.5) even in the presence of water.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.201601111</identifier><identifier>PMID: 27562692</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>amides ; Chemistry ; neighboring-group effects ; regioselectivity ; scandium ; transesterification</subject><ispartof>Chemistry, an Asian journal, 2016-10, Vol.11 (20), p.2859-2862</ispartof><rights>2016 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4481-dcff7b7826589f2dbf8982f3b5e852910bb04a8814ce30d47a480a5cfbb92d593</citedby><cites>FETCH-LOGICAL-c4481-dcff7b7826589f2dbf8982f3b5e852910bb04a8814ce30d47a480a5cfbb92d593</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fasia.201601111$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.201601111$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27562692$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wojtas, K. Philip</creatorcontrib><creatorcontrib>Lu, Jin-Yong</creatorcontrib><creatorcontrib>Krahn, Daniel</creatorcontrib><creatorcontrib>Arndt, Hans-Dieter</creatorcontrib><title>Regioselective Functionalization of 3-Hydroxy-pyridine Carboxylates by Neighboring Group Assistance</title><title>Chemistry, an Asian journal</title><addtitle>Chem. Asian J</addtitle><description>Regioselective hydrolysis, transesterification, and aminolysis of unactivated, highly substituted pyridine esters were realized under mild conditions by employing neighboring group assisted catalysis. Excellent yields were achieved without active removal of the alcohol byproduct. Regioselective aminolysis had a considerable substrate scope ([hetero]aryl, alkyl and amino acid). A mechanism involving assistance by the deprotonated phenolic OH‐group is suggested for hydrolysis and transesterification.
An unexpected docking site. Free phenolic hydroxy groups in pyridine rings were found to assist the regioselective transformation of proximal ester groups. Selective hydrolysis, transesterification, and amide bond formation can such be realized at very mild pH (8.5) even in the presence of water.</description><subject>amides</subject><subject>Chemistry</subject><subject>neighboring-group effects</subject><subject>regioselectivity</subject><subject>scandium</subject><subject>transesterification</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkM9v0zAYhi3ExMbgyhFF4sIlxT8T-1hVLB0amwZDcLNs50vxSONiN7Dw1-PSrUJc8MWvrOd9JT8IvSB4RjCmb0zyZkYxqTDJ5xE6IbIiJa_Jl8eHTOUxeprSLcaCYiWfoGNai4pWip4g9wFWPiTowW39DyjOxiGHMJje_zK7UISuYOVyamO4m8rNFH3rBygWJtr80JstpMJOxSX41Vcboh9WRRPDuCnmKfm0NYODZ-ioM32C5_f3Kfp09vZmsSwvrprzxfyidJxLUrau62pbS1oJqTra2k4qSTtmBUhBFcHWYm6kJNwBwy2vDZfYCNdZq2grFDtFr_e7mxi-j5C2eu2Tg743A4QxaSKZ4LKquMzoq3_Q2zDG_Os_FCaCK8YyNdtTLoaUInR6E_3axEkTrHf69U6_PujPhZf3s6NdQ3vAH3xnQO2Bn76H6T9zev7xfP73eLnvZq1wd-ia-E1XNauF_nzZ6Hc31837ZVNrxX4D5Auhgw</recordid><startdate>20161020</startdate><enddate>20161020</enddate><creator>Wojtas, K. Philip</creator><creator>Lu, Jin-Yong</creator><creator>Krahn, Daniel</creator><creator>Arndt, Hans-Dieter</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20161020</creationdate><title>Regioselective Functionalization of 3-Hydroxy-pyridine Carboxylates by Neighboring Group Assistance</title><author>Wojtas, K. Philip ; Lu, Jin-Yong ; Krahn, Daniel ; Arndt, Hans-Dieter</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4481-dcff7b7826589f2dbf8982f3b5e852910bb04a8814ce30d47a480a5cfbb92d593</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>amides</topic><topic>Chemistry</topic><topic>neighboring-group effects</topic><topic>regioselectivity</topic><topic>scandium</topic><topic>transesterification</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wojtas, K. Philip</creatorcontrib><creatorcontrib>Lu, Jin-Yong</creatorcontrib><creatorcontrib>Krahn, Daniel</creatorcontrib><creatorcontrib>Arndt, Hans-Dieter</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wojtas, K. Philip</au><au>Lu, Jin-Yong</au><au>Krahn, Daniel</au><au>Arndt, Hans-Dieter</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regioselective Functionalization of 3-Hydroxy-pyridine Carboxylates by Neighboring Group Assistance</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chem. Asian J</addtitle><date>2016-10-20</date><risdate>2016</risdate><volume>11</volume><issue>20</issue><spage>2859</spage><epage>2862</epage><pages>2859-2862</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>Regioselective hydrolysis, transesterification, and aminolysis of unactivated, highly substituted pyridine esters were realized under mild conditions by employing neighboring group assisted catalysis. Excellent yields were achieved without active removal of the alcohol byproduct. Regioselective aminolysis had a considerable substrate scope ([hetero]aryl, alkyl and amino acid). A mechanism involving assistance by the deprotonated phenolic OH‐group is suggested for hydrolysis and transesterification.
An unexpected docking site. Free phenolic hydroxy groups in pyridine rings were found to assist the regioselective transformation of proximal ester groups. Selective hydrolysis, transesterification, and amide bond formation can such be realized at very mild pH (8.5) even in the presence of water.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27562692</pmid><doi>10.1002/asia.201601111</doi><tpages>4</tpages></addata></record> |
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| source | Wiley Journals |
| subjects | amides Chemistry neighboring-group effects regioselectivity scandium transesterification |
| title | Regioselective Functionalization of 3-Hydroxy-pyridine Carboxylates by Neighboring Group Assistance |
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