Structure and Additive-free Transamidation of Planar N‑Cyano Amides
Although transamidation of amides generally requires metals, additives, or harsh conditions, we present here a facile transamidation of N-cyano amides with various amines at ambient temperature without any additive. N-cyano amides preferred the trans conformation and have a reduced double bond chara...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2023-05, Vol.88 (9), p.5704-5712 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 5712 |
|---|---|
| container_issue | 9 |
| container_start_page | 5704 |
| container_title | Journal of organic chemistry |
| container_volume | 88 |
| creator | Yamasaki, Ryu Okada, Yuko Iizumi, Hiromi Ito, Ai Fukuda, Kazuo Okamoto, Iwao |
| description | Although transamidation of amides generally requires metals, additives, or harsh conditions, we present here a facile transamidation of N-cyano amides with various amines at ambient temperature without any additive. N-cyano amides preferred the trans conformation and have a reduced double bond character revealed by crystal analysis. The DFT study indicates that the transamidation reaction proceeds through the direct attack of amine on the amide carbonyl since the LUMO (or LUMO+1) is located at the carbonyl moiety. |
| doi_str_mv | 10.1021/acs.joc.3c00172 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2806075038</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2806075038</sourcerecordid><originalsourceid>FETCH-LOGICAL-a333t-d46ecd3166e8d9cc49a8b8704e2ec86d4f1bf654cc7c51fba7452e33c7b0658f3</originalsourceid><addsrcrecordid>eNp1kE1Lw0AQhhdRbK2evUmOgqSd_UxyLKV-QFHBel42-wEpTVJ3E6E3_4J_0V_iSqo35zKHeeZl5kHoEsMUA8EzpcN00-op1QA4I0dojDmBVBTAjtEYgJCUEkFH6CyEDcTinJ-iEc2gYISzMVq-dL7XXe9tohqTzI2puurdps5bm6y9aoKqK6O6qm2S1iXPW9Uonzx-fXwu9qppk3mc2nCOTpzaBntx6BP0ertcL-7T1dPdw2K-ShWltEsNE1YbioWwuSm0ZoXKyzwDZonVuTDM4dIJzrTONMeuVBnjxFKqsxIEzx2doOshd-fbt96GTtZV0HYbr7JtHyTJQUDGgeYRnQ2o9m0I3jq581Wt_F5ikD_uZHQnozt5cBc3rg7hfVlb88f_yorAzQAMm71v4q__xn0DmMZ6aA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2806075038</pqid></control><display><type>article</type><title>Structure and Additive-free Transamidation of Planar N‑Cyano Amides</title><source>American Chemical Society Journals</source><creator>Yamasaki, Ryu ; Okada, Yuko ; Iizumi, Hiromi ; Ito, Ai ; Fukuda, Kazuo ; Okamoto, Iwao</creator><creatorcontrib>Yamasaki, Ryu ; Okada, Yuko ; Iizumi, Hiromi ; Ito, Ai ; Fukuda, Kazuo ; Okamoto, Iwao</creatorcontrib><description>Although transamidation of amides generally requires metals, additives, or harsh conditions, we present here a facile transamidation of N-cyano amides with various amines at ambient temperature without any additive. N-cyano amides preferred the trans conformation and have a reduced double bond character revealed by crystal analysis. The DFT study indicates that the transamidation reaction proceeds through the direct attack of amine on the amide carbonyl since the LUMO (or LUMO+1) is located at the carbonyl moiety.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.3c00172</identifier><identifier>PMID: 37094254</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2023-05, Vol.88 (9), p.5704-5712</ispartof><rights>2023 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-d46ecd3166e8d9cc49a8b8704e2ec86d4f1bf654cc7c51fba7452e33c7b0658f3</citedby><cites>FETCH-LOGICAL-a333t-d46ecd3166e8d9cc49a8b8704e2ec86d4f1bf654cc7c51fba7452e33c7b0658f3</cites><orcidid>0000-0001-6051-0879 ; 0000-0002-8976-2962 ; 0000-0003-0797-1478</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.3c00172$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.3c00172$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37094254$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yamasaki, Ryu</creatorcontrib><creatorcontrib>Okada, Yuko</creatorcontrib><creatorcontrib>Iizumi, Hiromi</creatorcontrib><creatorcontrib>Ito, Ai</creatorcontrib><creatorcontrib>Fukuda, Kazuo</creatorcontrib><creatorcontrib>Okamoto, Iwao</creatorcontrib><title>Structure and Additive-free Transamidation of Planar N‑Cyano Amides</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Although transamidation of amides generally requires metals, additives, or harsh conditions, we present here a facile transamidation of N-cyano amides with various amines at ambient temperature without any additive. N-cyano amides preferred the trans conformation and have a reduced double bond character revealed by crystal analysis. The DFT study indicates that the transamidation reaction proceeds through the direct attack of amine on the amide carbonyl since the LUMO (or LUMO+1) is located at the carbonyl moiety.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp1kE1Lw0AQhhdRbK2evUmOgqSd_UxyLKV-QFHBel42-wEpTVJ3E6E3_4J_0V_iSqo35zKHeeZl5kHoEsMUA8EzpcN00-op1QA4I0dojDmBVBTAjtEYgJCUEkFH6CyEDcTinJ-iEc2gYISzMVq-dL7XXe9tohqTzI2puurdps5bm6y9aoKqK6O6qm2S1iXPW9Uonzx-fXwu9qppk3mc2nCOTpzaBntx6BP0ertcL-7T1dPdw2K-ShWltEsNE1YbioWwuSm0ZoXKyzwDZonVuTDM4dIJzrTONMeuVBnjxFKqsxIEzx2doOshd-fbt96GTtZV0HYbr7JtHyTJQUDGgeYRnQ2o9m0I3jq581Wt_F5ikD_uZHQnozt5cBc3rg7hfVlb88f_yorAzQAMm71v4q__xn0DmMZ6aA</recordid><startdate>20230505</startdate><enddate>20230505</enddate><creator>Yamasaki, Ryu</creator><creator>Okada, Yuko</creator><creator>Iizumi, Hiromi</creator><creator>Ito, Ai</creator><creator>Fukuda, Kazuo</creator><creator>Okamoto, Iwao</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6051-0879</orcidid><orcidid>https://orcid.org/0000-0002-8976-2962</orcidid><orcidid>https://orcid.org/0000-0003-0797-1478</orcidid></search><sort><creationdate>20230505</creationdate><title>Structure and Additive-free Transamidation of Planar N‑Cyano Amides</title><author>Yamasaki, Ryu ; Okada, Yuko ; Iizumi, Hiromi ; Ito, Ai ; Fukuda, Kazuo ; Okamoto, Iwao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-d46ecd3166e8d9cc49a8b8704e2ec86d4f1bf654cc7c51fba7452e33c7b0658f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yamasaki, Ryu</creatorcontrib><creatorcontrib>Okada, Yuko</creatorcontrib><creatorcontrib>Iizumi, Hiromi</creatorcontrib><creatorcontrib>Ito, Ai</creatorcontrib><creatorcontrib>Fukuda, Kazuo</creatorcontrib><creatorcontrib>Okamoto, Iwao</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yamasaki, Ryu</au><au>Okada, Yuko</au><au>Iizumi, Hiromi</au><au>Ito, Ai</au><au>Fukuda, Kazuo</au><au>Okamoto, Iwao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure and Additive-free Transamidation of Planar N‑Cyano Amides</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2023-05-05</date><risdate>2023</risdate><volume>88</volume><issue>9</issue><spage>5704</spage><epage>5712</epage><pages>5704-5712</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Although transamidation of amides generally requires metals, additives, or harsh conditions, we present here a facile transamidation of N-cyano amides with various amines at ambient temperature without any additive. N-cyano amides preferred the trans conformation and have a reduced double bond character revealed by crystal analysis. The DFT study indicates that the transamidation reaction proceeds through the direct attack of amine on the amide carbonyl since the LUMO (or LUMO+1) is located at the carbonyl moiety.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>37094254</pmid><doi>10.1021/acs.joc.3c00172</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-6051-0879</orcidid><orcidid>https://orcid.org/0000-0002-8976-2962</orcidid><orcidid>https://orcid.org/0000-0003-0797-1478</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2023-05, Vol.88 (9), p.5704-5712 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2806075038 |
| source | American Chemical Society Journals |
| title | Structure and Additive-free Transamidation of Planar N‑Cyano Amides |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-11T12%3A54%3A37IST&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=Structure%20and%20Additive-free%20Transamidation%20of%20Planar%20N%E2%80%91Cyano%20Amides&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Yamasaki,%20Ryu&rft.date=2023-05-05&rft.volume=88&rft.issue=9&rft.spage=5704&rft.epage=5712&rft.pages=5704-5712&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.3c00172&rft_dat=%3Cproquest_cross%3E2806075038%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=2806075038&rft_id=info:pmid/37094254&rfr_iscdi=true |