Copper-Catalyzed Three-Component Reaction: Solvent-Controlled Regioselective Synthesis of 4‑Amino- and 6‑Amino-2-iminopyridines
Regioselective synthesis of multisubstituted 4-amino- and 6-amino-2-iminopyridines has been developed via the copper-catalyzed three-component reaction based on the reaction conditions selection. The reaction of sulfonyl azides, alkynes, and 2-[(amino)methylene]malononitriles catalyzed by copper(I)...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2013-11, Vol.15 (22), p.5786-5789 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 5789 |
|---|---|
| container_issue | 22 |
| container_start_page | 5786 |
| container_title | Organic letters |
| container_volume | 15 |
| creator | Zhou, Fenguo Liu, Xu Zhang, Ning Liang, Yongjiu Zhang, Rui Xin, Xiaoqing Dong, Dewen |
| description | Regioselective synthesis of multisubstituted 4-amino- and 6-amino-2-iminopyridines has been developed via the copper-catalyzed three-component reaction based on the reaction conditions selection. The reaction of sulfonyl azides, alkynes, and 2-[(amino)methylene]malononitriles catalyzed by copper(I) iodide in tetrahydrofuran at room temperature afforded substituted 4-amino-2-iminopyridines, whereas, in N,N-dimethylformamide at 50 °C under N2, it generated substituted 6-amino-2-iminopyridines as predominant products. |
| doi_str_mv | 10.1021/ol4028368 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1459151671</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1459151671</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-383de85ccf72cb6bc212bc2de18807f37c0c7708feef36c5615dfc1e66c1ab953</originalsourceid><addsrcrecordid>eNptkMtKxDAUhoMoXkYXvoB0I-iimpO2acbdULyBIIy6Lpn0VCNpUpOOMK4En8BX9EmMjM7KzfnP5eOH8xOyD_QEKINTZ3LKRMbFGtmGgmVpSQu2vuo53SI7ITxTCnEz3iRbLIcScia2yUfl-h59WslBmsUbNsn9k0dMK9f1zqIdkilKNWhnz5I7Z17jJt7s4J0xEZ7io3YBDUbkFZO7hR2eMOiQuDbJv94_J522Lk2kbRK-Glmqf7RfeN1oi2GXbLTSBNz71RF5uDi_r67Sm9vL62pyk8pMwJBmImtQFEq1JVMzPlMMWCwNghC0bLNSUVWWVLSIbcZVwaFoWgXIuQI5GxfZiBwtfXvvXuYYhrrTQaEx0qKbhxryYgwF8BIierxElXcheGzr3utO-kUNtP7JvF5lHtmDX9v5rMNmRf6FHIHDJSBVqJ_d3Nv45T9G36R3i5I</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1459151671</pqid></control><display><type>article</type><title>Copper-Catalyzed Three-Component Reaction: Solvent-Controlled Regioselective Synthesis of 4‑Amino- and 6‑Amino-2-iminopyridines</title><source>MEDLINE</source><source>ACS Publications</source><creator>Zhou, Fenguo ; Liu, Xu ; Zhang, Ning ; Liang, Yongjiu ; Zhang, Rui ; Xin, Xiaoqing ; Dong, Dewen</creator><creatorcontrib>Zhou, Fenguo ; Liu, Xu ; Zhang, Ning ; Liang, Yongjiu ; Zhang, Rui ; Xin, Xiaoqing ; Dong, Dewen</creatorcontrib><description>Regioselective synthesis of multisubstituted 4-amino- and 6-amino-2-iminopyridines has been developed via the copper-catalyzed three-component reaction based on the reaction conditions selection. The reaction of sulfonyl azides, alkynes, and 2-[(amino)methylene]malononitriles catalyzed by copper(I) iodide in tetrahydrofuran at room temperature afforded substituted 4-amino-2-iminopyridines, whereas, in N,N-dimethylformamide at 50 °C under N2, it generated substituted 6-amino-2-iminopyridines as predominant products.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol4028368</identifier><identifier>PMID: 24171428</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Catalysis ; Copper - chemistry ; Molecular Structure ; Nitriles - chemistry ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Solvents - chemistry</subject><ispartof>Organic letters, 2013-11, Vol.15 (22), p.5786-5789</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-383de85ccf72cb6bc212bc2de18807f37c0c7708feef36c5615dfc1e66c1ab953</citedby><cites>FETCH-LOGICAL-a381t-383de85ccf72cb6bc212bc2de18807f37c0c7708feef36c5615dfc1e66c1ab953</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/ol4028368$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol4028368$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27059,27907,27908,56721,56771</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24171428$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhou, Fenguo</creatorcontrib><creatorcontrib>Liu, Xu</creatorcontrib><creatorcontrib>Zhang, Ning</creatorcontrib><creatorcontrib>Liang, Yongjiu</creatorcontrib><creatorcontrib>Zhang, Rui</creatorcontrib><creatorcontrib>Xin, Xiaoqing</creatorcontrib><creatorcontrib>Dong, Dewen</creatorcontrib><title>Copper-Catalyzed Three-Component Reaction: Solvent-Controlled Regioselective Synthesis of 4‑Amino- and 6‑Amino-2-iminopyridines</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Regioselective synthesis of multisubstituted 4-amino- and 6-amino-2-iminopyridines has been developed via the copper-catalyzed three-component reaction based on the reaction conditions selection. The reaction of sulfonyl azides, alkynes, and 2-[(amino)methylene]malononitriles catalyzed by copper(I) iodide in tetrahydrofuran at room temperature afforded substituted 4-amino-2-iminopyridines, whereas, in N,N-dimethylformamide at 50 °C under N2, it generated substituted 6-amino-2-iminopyridines as predominant products.</description><subject>Catalysis</subject><subject>Copper - chemistry</subject><subject>Molecular Structure</subject><subject>Nitriles - chemistry</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Solvents - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtKxDAUhoMoXkYXvoB0I-iimpO2acbdULyBIIy6Lpn0VCNpUpOOMK4En8BX9EmMjM7KzfnP5eOH8xOyD_QEKINTZ3LKRMbFGtmGgmVpSQu2vuo53SI7ITxTCnEz3iRbLIcScia2yUfl-h59WslBmsUbNsn9k0dMK9f1zqIdkilKNWhnz5I7Z17jJt7s4J0xEZ7io3YBDUbkFZO7hR2eMOiQuDbJv94_J522Lk2kbRK-Glmqf7RfeN1oi2GXbLTSBNz71RF5uDi_r67Sm9vL62pyk8pMwJBmImtQFEq1JVMzPlMMWCwNghC0bLNSUVWWVLSIbcZVwaFoWgXIuQI5GxfZiBwtfXvvXuYYhrrTQaEx0qKbhxryYgwF8BIierxElXcheGzr3utO-kUNtP7JvF5lHtmDX9v5rMNmRf6FHIHDJSBVqJ_d3Nv45T9G36R3i5I</recordid><startdate>20131115</startdate><enddate>20131115</enddate><creator>Zhou, Fenguo</creator><creator>Liu, Xu</creator><creator>Zhang, Ning</creator><creator>Liang, Yongjiu</creator><creator>Zhang, Rui</creator><creator>Xin, Xiaoqing</creator><creator>Dong, Dewen</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></search><sort><creationdate>20131115</creationdate><title>Copper-Catalyzed Three-Component Reaction: Solvent-Controlled Regioselective Synthesis of 4‑Amino- and 6‑Amino-2-iminopyridines</title><author>Zhou, Fenguo ; Liu, Xu ; Zhang, Ning ; Liang, Yongjiu ; Zhang, Rui ; Xin, Xiaoqing ; Dong, Dewen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-383de85ccf72cb6bc212bc2de18807f37c0c7708feef36c5615dfc1e66c1ab953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Catalysis</topic><topic>Copper - chemistry</topic><topic>Molecular Structure</topic><topic>Nitriles - chemistry</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><topic>Solvents - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhou, Fenguo</creatorcontrib><creatorcontrib>Liu, Xu</creatorcontrib><creatorcontrib>Zhang, Ning</creatorcontrib><creatorcontrib>Liang, Yongjiu</creatorcontrib><creatorcontrib>Zhang, Rui</creatorcontrib><creatorcontrib>Xin, Xiaoqing</creatorcontrib><creatorcontrib>Dong, Dewen</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><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhou, Fenguo</au><au>Liu, Xu</au><au>Zhang, Ning</au><au>Liang, Yongjiu</au><au>Zhang, Rui</au><au>Xin, Xiaoqing</au><au>Dong, Dewen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-Catalyzed Three-Component Reaction: Solvent-Controlled Regioselective Synthesis of 4‑Amino- and 6‑Amino-2-iminopyridines</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2013-11-15</date><risdate>2013</risdate><volume>15</volume><issue>22</issue><spage>5786</spage><epage>5789</epage><pages>5786-5789</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Regioselective synthesis of multisubstituted 4-amino- and 6-amino-2-iminopyridines has been developed via the copper-catalyzed three-component reaction based on the reaction conditions selection. The reaction of sulfonyl azides, alkynes, and 2-[(amino)methylene]malononitriles catalyzed by copper(I) iodide in tetrahydrofuran at room temperature afforded substituted 4-amino-2-iminopyridines, whereas, in N,N-dimethylformamide at 50 °C under N2, it generated substituted 6-amino-2-iminopyridines as predominant products.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24171428</pmid><doi>10.1021/ol4028368</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2013-11, Vol.15 (22), p.5786-5789 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1459151671 |
| source | MEDLINE; ACS Publications |
| subjects | Catalysis Copper - chemistry Molecular Structure Nitriles - chemistry Pyridines - chemical synthesis Pyridines - chemistry Solvents - chemistry |
| title | Copper-Catalyzed Three-Component Reaction: Solvent-Controlled Regioselective Synthesis of 4‑Amino- and 6‑Amino-2-iminopyridines |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-16T08%3A45%3A40IST&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=Copper-Catalyzed%20Three-Component%20Reaction:%20Solvent-Controlled%20Regioselective%20Synthesis%20of%204%E2%80%91Amino-%20and%206%E2%80%91Amino-2-iminopyridines&rft.jtitle=Organic%20letters&rft.au=Zhou,%20Fenguo&rft.date=2013-11-15&rft.volume=15&rft.issue=22&rft.spage=5786&rft.epage=5789&rft.pages=5786-5789&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol4028368&rft_dat=%3Cproquest_cross%3E1459151671%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=1459151671&rft_id=info:pmid/24171428&rfr_iscdi=true |