Triflic Acid-Promoted 1,2-Amino Migration Reactions in α‑Arylaminoacrylamides: Access to Substituted β‑Aminoamides
A straightforward synthesis of substituted β-aminoamides from α-arylamino-β-hydroxyacrylamides, α-arylamino-β-oxoamides, or their tautomeric mixture has been described. The (E)-enol triflate intermediates are readily generated in situ from these substrates in the presence of triflic anhydride (Tf2O)...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2024-06, Vol.89 (12), p.8861-8870 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 8870 |
|---|---|
| container_issue | 12 |
| container_start_page | 8861 |
| container_title | Journal of organic chemistry |
| container_volume | 89 |
| creator | Li, Jiawang Wang, Yu Zhang, Rui Li, Jiacheng Dong, Dewen |
| description | A straightforward synthesis of substituted β-aminoamides from α-arylamino-β-hydroxyacrylamides, α-arylamino-β-oxoamides, or their tautomeric mixture has been described. The (E)-enol triflate intermediates are readily generated in situ from these substrates in the presence of triflic anhydride (Tf2O) and triethylamine (Et3N) in a chemoselective manner and undergo triflic acid (TfOH)-promoted cyclization and ring-opening reactions with alcohols to deliver the desired products. The one-pot two-step synthetic protocol features the use of readily available starting materials, mild reaction conditions, high chemoselectivity, operational simplicity, and a wide range of synthetic potential of the products. |
| doi_str_mv | 10.1021/acs.joc.4c00731 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_3065985489</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3153642685</sourcerecordid><originalsourceid>FETCH-LOGICAL-a320t-639a0a89ef987286f2c6e0980743ba66e85a0b3e3d5d549e1709a7ed1f20b1bf3</originalsourceid><addsrcrecordid>eNqFkTtOxTAQRS0EgsenpkMpkSCPsR07Nt0T4ieBQHzqyHEcZJTEYCcSdGyBpcBCWAQrISEPOsQ0M8W5t5iD0CaGKQaC95QO03unp4kGSCleQBPMCMRcQrKIJgCExJRwuoJWQ7iHfhhjy2iFCpEwDMkEPd14W1ZWRzNti_jSu9q1pojwLolntW1cdG7vvGqta6Iro_RwhMg20cfb58vrzD9XaqCUHq_ChP2-SZsQotZF110eWtt2Q-PH-xD4hr-5dbRUqiqYjfleQ7dHhzcHJ_HZxfHpwewsVpRAG3MqFSghTSlFSgQvieYGpIA0obni3AimIKeGFqxgiTQ4BalSU-CSQI7zkq6h7bH3wbvHzoQ2q23QpqpUY1wXMooZ5Qnhgv2PAmdSsETIHt0bUe1dCN6U2YO3tfLPGYZsMJP1ZrLeTDY30ye25uVdXpvil_9R0QM7IzAmO9_0b_mz7gtbfZyu</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3065985489</pqid></control><display><type>article</type><title>Triflic Acid-Promoted 1,2-Amino Migration Reactions in α‑Arylaminoacrylamides: Access to Substituted β‑Aminoamides</title><source>ACS Publications</source><creator>Li, Jiawang ; Wang, Yu ; Zhang, Rui ; Li, Jiacheng ; Dong, Dewen</creator><creatorcontrib>Li, Jiawang ; Wang, Yu ; Zhang, Rui ; Li, Jiacheng ; Dong, Dewen</creatorcontrib><description>A straightforward synthesis of substituted β-aminoamides from α-arylamino-β-hydroxyacrylamides, α-arylamino-β-oxoamides, or their tautomeric mixture has been described. The (E)-enol triflate intermediates are readily generated in situ from these substrates in the presence of triflic anhydride (Tf2O) and triethylamine (Et3N) in a chemoselective manner and undergo triflic acid (TfOH)-promoted cyclization and ring-opening reactions with alcohols to deliver the desired products. The one-pot two-step synthetic protocol features the use of readily available starting materials, mild reaction conditions, high chemoselectivity, operational simplicity, and a wide range of synthetic potential of the products.</description><identifier>ISSN: 0022-3263</identifier><identifier>ISSN: 1520-6904</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.4c00731</identifier><identifier>PMID: 38845104</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>anhydrides ; chemoselectivity ; organic chemistry ; triethylamine</subject><ispartof>Journal of organic chemistry, 2024-06, Vol.89 (12), p.8861-8870</ispartof><rights>2024 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a320t-639a0a89ef987286f2c6e0980743ba66e85a0b3e3d5d549e1709a7ed1f20b1bf3</cites><orcidid>0000-0003-1477-8422</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.4c00731$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.4c00731$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38845104$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Jiawang</creatorcontrib><creatorcontrib>Wang, Yu</creatorcontrib><creatorcontrib>Zhang, Rui</creatorcontrib><creatorcontrib>Li, Jiacheng</creatorcontrib><creatorcontrib>Dong, Dewen</creatorcontrib><title>Triflic Acid-Promoted 1,2-Amino Migration Reactions in α‑Arylaminoacrylamides: Access to Substituted β‑Aminoamides</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A straightforward synthesis of substituted β-aminoamides from α-arylamino-β-hydroxyacrylamides, α-arylamino-β-oxoamides, or their tautomeric mixture has been described. The (E)-enol triflate intermediates are readily generated in situ from these substrates in the presence of triflic anhydride (Tf2O) and triethylamine (Et3N) in a chemoselective manner and undergo triflic acid (TfOH)-promoted cyclization and ring-opening reactions with alcohols to deliver the desired products. The one-pot two-step synthetic protocol features the use of readily available starting materials, mild reaction conditions, high chemoselectivity, operational simplicity, and a wide range of synthetic potential of the products.</description><subject>anhydrides</subject><subject>chemoselectivity</subject><subject>organic chemistry</subject><subject>triethylamine</subject><issn>0022-3263</issn><issn>1520-6904</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkTtOxTAQRS0EgsenpkMpkSCPsR07Nt0T4ieBQHzqyHEcZJTEYCcSdGyBpcBCWAQrISEPOsQ0M8W5t5iD0CaGKQaC95QO03unp4kGSCleQBPMCMRcQrKIJgCExJRwuoJWQ7iHfhhjy2iFCpEwDMkEPd14W1ZWRzNti_jSu9q1pojwLolntW1cdG7vvGqta6Iro_RwhMg20cfb58vrzD9XaqCUHq_ChP2-SZsQotZF110eWtt2Q-PH-xD4hr-5dbRUqiqYjfleQ7dHhzcHJ_HZxfHpwewsVpRAG3MqFSghTSlFSgQvieYGpIA0obni3AimIKeGFqxgiTQ4BalSU-CSQI7zkq6h7bH3wbvHzoQ2q23QpqpUY1wXMooZ5Qnhgv2PAmdSsETIHt0bUe1dCN6U2YO3tfLPGYZsMJP1ZrLeTDY30ye25uVdXpvil_9R0QM7IzAmO9_0b_mz7gtbfZyu</recordid><startdate>20240621</startdate><enddate>20240621</enddate><creator>Li, Jiawang</creator><creator>Wang, Yu</creator><creator>Zhang, Rui</creator><creator>Li, Jiacheng</creator><creator>Dong, Dewen</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0003-1477-8422</orcidid></search><sort><creationdate>20240621</creationdate><title>Triflic Acid-Promoted 1,2-Amino Migration Reactions in α‑Arylaminoacrylamides: Access to Substituted β‑Aminoamides</title><author>Li, Jiawang ; Wang, Yu ; Zhang, Rui ; Li, Jiacheng ; Dong, Dewen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a320t-639a0a89ef987286f2c6e0980743ba66e85a0b3e3d5d549e1709a7ed1f20b1bf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>anhydrides</topic><topic>chemoselectivity</topic><topic>organic chemistry</topic><topic>triethylamine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Jiawang</creatorcontrib><creatorcontrib>Wang, Yu</creatorcontrib><creatorcontrib>Zhang, Rui</creatorcontrib><creatorcontrib>Li, Jiacheng</creatorcontrib><creatorcontrib>Dong, Dewen</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Jiawang</au><au>Wang, Yu</au><au>Zhang, Rui</au><au>Li, Jiacheng</au><au>Dong, Dewen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Triflic Acid-Promoted 1,2-Amino Migration Reactions in α‑Arylaminoacrylamides: Access to Substituted β‑Aminoamides</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2024-06-21</date><risdate>2024</risdate><volume>89</volume><issue>12</issue><spage>8861</spage><epage>8870</epage><pages>8861-8870</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><abstract>A straightforward synthesis of substituted β-aminoamides from α-arylamino-β-hydroxyacrylamides, α-arylamino-β-oxoamides, or their tautomeric mixture has been described. The (E)-enol triflate intermediates are readily generated in situ from these substrates in the presence of triflic anhydride (Tf2O) and triethylamine (Et3N) in a chemoselective manner and undergo triflic acid (TfOH)-promoted cyclization and ring-opening reactions with alcohols to deliver the desired products. The one-pot two-step synthetic protocol features the use of readily available starting materials, mild reaction conditions, high chemoselectivity, operational simplicity, and a wide range of synthetic potential of the products.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>38845104</pmid><doi>10.1021/acs.joc.4c00731</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0003-1477-8422</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2024-06, Vol.89 (12), p.8861-8870 |
| issn | 0022-3263 1520-6904 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_3065985489 |
| source | ACS Publications |
| subjects | anhydrides chemoselectivity organic chemistry triethylamine |
| title | Triflic Acid-Promoted 1,2-Amino Migration Reactions in α‑Arylaminoacrylamides: Access to Substituted β‑Aminoamides |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-18T16%3A46%3A27IST&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=Triflic%20Acid-Promoted%201,2-Amino%20Migration%20Reactions%20in%20%CE%B1%E2%80%91Arylaminoacrylamides:%20Access%20to%20Substituted%20%CE%B2%E2%80%91Aminoamides&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Li,%20Jiawang&rft.date=2024-06-21&rft.volume=89&rft.issue=12&rft.spage=8861&rft.epage=8870&rft.pages=8861-8870&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.4c00731&rft_dat=%3Cproquest_cross%3E3153642685%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=3065985489&rft_id=info:pmid/38845104&rfr_iscdi=true |