Annulation of Thioimidates and Vinyl Carbodiimides to Prepare 2-Aminopyrimidines, Competent Nucleophiles for Intramolecular Alkyne Hydroamination. Synthesis of (−)-Crambidine
A convergent synthesis of (−)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles.
Gespeichert in:
| Veröffentlicht in: | Journal of the American Chemical Society 2010-02, Vol.132 (6), p.1802-1803 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1803 |
|---|---|
| container_issue | 6 |
| container_start_page | 1802 |
| container_title | Journal of the American Chemical Society |
| container_volume | 132 |
| creator | Perl, Nicholas R Ide, Nathan D Prajapati, Sudeep Perfect, Hahdi H Durón, Sergio G Gin, David Y |
| description | A convergent synthesis of (−)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles. |
| doi_str_mv | 10.1021/ja910831k |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_2839241</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>733718617</sourcerecordid><originalsourceid>FETCH-LOGICAL-a385k-e83f2f4ec29a5f1a90e03cb3a8fb68cc0d6cb3545a9ea7032e87d98864c796ce3</originalsourceid><addsrcrecordid>eNptUd2K1DAYDaK44-qFLyC5EV2wa36mbXojDEXdhUUFV29Dmn51MpMmNWmFvoHXPonP5JOY7qyDgrkJ33fOd85JPoQeU3JOCaMvd6qiRHC6v4NWNGckyykr7qIVIYRlpSj4CXoQ4y6VaybofXTCCKnydFbo58a5yarReId9h6-3xpvetGqEiJVr8WfjZotrFRrfmgVJ_dHjDwEGFQCzbNMb54c5LJhxEF_g2vcDjOBG_G7SFvywNTZNdT7gSzcG1XsLOnkGvLH72QG-mNvgVdK5iXGOP85u3EI0cUn0_Nf3H2dZncaaG4OH6F6nbIRHt_cp-vTm9XV9kV29f3tZb64yxUW-z0DwjnVr0KxSeUdVRYBw3XAluqYQWpO2SFW-zlUFqiScgSjbSohircuq0MBP0auD7jA1PbQaluhWDumhKszSKyP_RZzZyi_-m2SCV2xNk8CzW4Hgv04QR9mbqMFa5cBPUZacl1QUtEzMswNTBx9jgO7oQolcFiyPC07cJ3_HOjL_bDQRnh4ISke581Nw6Zf-I_QbCfazKg</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>733718617</pqid></control><display><type>article</type><title>Annulation of Thioimidates and Vinyl Carbodiimides to Prepare 2-Aminopyrimidines, Competent Nucleophiles for Intramolecular Alkyne Hydroamination. Synthesis of (−)-Crambidine</title><source>ACS Publications</source><source>MEDLINE</source><creator>Perl, Nicholas R ; Ide, Nathan D ; Prajapati, Sudeep ; Perfect, Hahdi H ; Durón, Sergio G ; Gin, David Y</creator><creatorcontrib>Perl, Nicholas R ; Ide, Nathan D ; Prajapati, Sudeep ; Perfect, Hahdi H ; Durón, Sergio G ; Gin, David Y</creatorcontrib><description>A convergent synthesis of (−)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja910831k</identifier><identifier>PMID: 20095555</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkynes - chemistry ; Amination ; Carbodiimides - chemistry ; Guanidine - analogs & derivatives ; Guanidine - chemical synthesis ; Guanidine - chemistry ; Imidoesters - chemistry ; Pyrimidines - chemistry ; Spiro Compounds - chemical synthesis ; Spiro Compounds - chemistry ; Stereoisomerism</subject><ispartof>Journal of the American Chemical Society, 2010-02, Vol.132 (6), p.1802-1803</ispartof><rights>Copyright © 2010 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a385k-e83f2f4ec29a5f1a90e03cb3a8fb68cc0d6cb3545a9ea7032e87d98864c796ce3</citedby><cites>FETCH-LOGICAL-a385k-e83f2f4ec29a5f1a90e03cb3a8fb68cc0d6cb3545a9ea7032e87d98864c796ce3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja910831k$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja910831k$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20095555$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Perl, Nicholas R</creatorcontrib><creatorcontrib>Ide, Nathan D</creatorcontrib><creatorcontrib>Prajapati, Sudeep</creatorcontrib><creatorcontrib>Perfect, Hahdi H</creatorcontrib><creatorcontrib>Durón, Sergio G</creatorcontrib><creatorcontrib>Gin, David Y</creatorcontrib><title>Annulation of Thioimidates and Vinyl Carbodiimides to Prepare 2-Aminopyrimidines, Competent Nucleophiles for Intramolecular Alkyne Hydroamination. Synthesis of (−)-Crambidine</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>A convergent synthesis of (−)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles.</description><subject>Alkynes - chemistry</subject><subject>Amination</subject><subject>Carbodiimides - chemistry</subject><subject>Guanidine - analogs & derivatives</subject><subject>Guanidine - chemical synthesis</subject><subject>Guanidine - chemistry</subject><subject>Imidoesters - chemistry</subject><subject>Pyrimidines - chemistry</subject><subject>Spiro Compounds - chemical synthesis</subject><subject>Spiro Compounds - chemistry</subject><subject>Stereoisomerism</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptUd2K1DAYDaK44-qFLyC5EV2wa36mbXojDEXdhUUFV29Dmn51MpMmNWmFvoHXPonP5JOY7qyDgrkJ33fOd85JPoQeU3JOCaMvd6qiRHC6v4NWNGckyykr7qIVIYRlpSj4CXoQ4y6VaybofXTCCKnydFbo58a5yarReId9h6-3xpvetGqEiJVr8WfjZotrFRrfmgVJ_dHjDwEGFQCzbNMb54c5LJhxEF_g2vcDjOBG_G7SFvywNTZNdT7gSzcG1XsLOnkGvLH72QG-mNvgVdK5iXGOP85u3EI0cUn0_Nf3H2dZncaaG4OH6F6nbIRHt_cp-vTm9XV9kV29f3tZb64yxUW-z0DwjnVr0KxSeUdVRYBw3XAluqYQWpO2SFW-zlUFqiScgSjbSohircuq0MBP0auD7jA1PbQaluhWDumhKszSKyP_RZzZyi_-m2SCV2xNk8CzW4Hgv04QR9mbqMFa5cBPUZacl1QUtEzMswNTBx9jgO7oQolcFiyPC07cJ3_HOjL_bDQRnh4ISke581Nw6Zf-I_QbCfazKg</recordid><startdate>20100217</startdate><enddate>20100217</enddate><creator>Perl, Nicholas R</creator><creator>Ide, Nathan D</creator><creator>Prajapati, Sudeep</creator><creator>Perfect, Hahdi H</creator><creator>Durón, Sergio G</creator><creator>Gin, David Y</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20100217</creationdate><title>Annulation of Thioimidates and Vinyl Carbodiimides to Prepare 2-Aminopyrimidines, Competent Nucleophiles for Intramolecular Alkyne Hydroamination. Synthesis of (−)-Crambidine</title><author>Perl, Nicholas R ; Ide, Nathan D ; Prajapati, Sudeep ; Perfect, Hahdi H ; Durón, Sergio G ; Gin, David Y</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a385k-e83f2f4ec29a5f1a90e03cb3a8fb68cc0d6cb3545a9ea7032e87d98864c796ce3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Alkynes - chemistry</topic><topic>Amination</topic><topic>Carbodiimides - chemistry</topic><topic>Guanidine - analogs & derivatives</topic><topic>Guanidine - chemical synthesis</topic><topic>Guanidine - chemistry</topic><topic>Imidoesters - chemistry</topic><topic>Pyrimidines - chemistry</topic><topic>Spiro Compounds - chemical synthesis</topic><topic>Spiro Compounds - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Perl, Nicholas R</creatorcontrib><creatorcontrib>Ide, Nathan D</creatorcontrib><creatorcontrib>Prajapati, Sudeep</creatorcontrib><creatorcontrib>Perfect, Hahdi H</creatorcontrib><creatorcontrib>Durón, Sergio G</creatorcontrib><creatorcontrib>Gin, David Y</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Perl, Nicholas R</au><au>Ide, Nathan D</au><au>Prajapati, Sudeep</au><au>Perfect, Hahdi H</au><au>Durón, Sergio G</au><au>Gin, David Y</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Annulation of Thioimidates and Vinyl Carbodiimides to Prepare 2-Aminopyrimidines, Competent Nucleophiles for Intramolecular Alkyne Hydroamination. Synthesis of (−)-Crambidine</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2010-02-17</date><risdate>2010</risdate><volume>132</volume><issue>6</issue><spage>1802</spage><epage>1803</epage><pages>1802-1803</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>A convergent synthesis of (−)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>20095555</pmid><doi>10.1021/ja910831k</doi><tpages>2</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 2010-02, Vol.132 (6), p.1802-1803 |
| issn | 0002-7863 1520-5126 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_2839241 |
| source | ACS Publications; MEDLINE |
| subjects | Alkynes - chemistry Amination Carbodiimides - chemistry Guanidine - analogs & derivatives Guanidine - chemical synthesis Guanidine - chemistry Imidoesters - chemistry Pyrimidines - chemistry Spiro Compounds - chemical synthesis Spiro Compounds - chemistry Stereoisomerism |
| title | Annulation of Thioimidates and Vinyl Carbodiimides to Prepare 2-Aminopyrimidines, Competent Nucleophiles for Intramolecular Alkyne Hydroamination. Synthesis of (−)-Crambidine |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-06T18%3A49%3A15IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Annulation%20of%20Thioimidates%20and%20Vinyl%20Carbodiimides%20to%20Prepare%202-Aminopyrimidines,%20Competent%20Nucleophiles%20for%20Intramolecular%20Alkyne%20Hydroamination.%20Synthesis%20of%20(%E2%88%92)-Crambidine&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Perl,%20Nicholas%20R&rft.date=2010-02-17&rft.volume=132&rft.issue=6&rft.spage=1802&rft.epage=1803&rft.pages=1802-1803&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/ja910831k&rft_dat=%3Cproquest_pubme%3E733718617%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=733718617&rft_id=info:pmid/20095555&rfr_iscdi=true |