Iron-Catalyzed Formation of 2‑Aminopyridines from Diynes and Cyanamides
Diynes and cyanamides undergo an iron-catalyzed [2 + 2 + 2] cycloaddition to form highly substituted 2-aminopyridines in an atom-efficient manner that is both high yielding and regioselective. This system was also used to cyclize two terminal alkynes and a cyanamide to afford a 2,4,6-trisubstituted...
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| Veröffentlicht in: | Journal of organic chemistry 2012-09, Vol.77 (17), p.7555-7563 |
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| container_end_page | 7563 |
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| container_issue | 17 |
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| container_title | Journal of organic chemistry |
| container_volume | 77 |
| creator | Lane, Timothy K D’Souza, Brendan R Louie, Janis |
| description | Diynes and cyanamides undergo an iron-catalyzed [2 + 2 + 2] cycloaddition to form highly substituted 2-aminopyridines in an atom-efficient manner that is both high yielding and regioselective. This system was also used to cyclize two terminal alkynes and a cyanamide to afford a 2,4,6-trisubstituted pyridine product regioselectively. |
| doi_str_mv | 10.1021/jo3012418 |
| format | Article |
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Org. Chem</addtitle><description>Diynes and cyanamides undergo an iron-catalyzed [2 + 2 + 2] cycloaddition to form highly substituted 2-aminopyridines in an atom-efficient manner that is both high yielding and regioselective. This system was also used to cyclize two terminal alkynes and a cyanamide to afford a 2,4,6-trisubstituted pyridine product regioselectively.</description><subject>alkynes</subject><subject>Aminopyridines - chemical synthesis</subject><subject>Aminopyridines - chemistry</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Cyanamide - chemistry</subject><subject>cyanamides</subject><subject>Cyclization</subject><subject>Diynes - chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Iron - chemistry</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>pyridines</subject><subject>regioselectivity</subject><issn>0022-3263</issn><issn>1520-6904</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc2KFDEUhYMoTju68AWkNoIuSm9uKqFqIwytow0DbnQdbudHM1QlbVItlCtfwVf0SczQbY-C4N3kQj5OTs5h7DGHFxyQv7xOAjh2vL_DVlwitGqA7i5bASC2ApU4Yw9KuYY6Usr77Ayx76RSasU2m5xiu6aZxuWbs81lyhPNIcUm-QZ_fv9xMYWYdksONkRXGp_T1LwOy81O0TbrhSJNwbrykN3zNBb36Hies4-Xbz6s37VX799u1hdXLUnRza1BVOA8yN4I2QH3ZKsVr6TjJAkMOWsEgjeD4QotWe62Bp3f8kF6Z1Gcs1cH3d1-O1XYxTnTqHc5TJQXnSjov29i-Kw_pa9adD0IPlSBZ0eBnL7sXZn1FIpx40jRpX3ReIhpkOq_KAfRq5oyyIo-P6Amp1Ky8ydHHPRNS_rUUmWf_PmFE_m7lgo8PQJUDI0-UzSh3HJKSOgGvOXIlKq_z7Em_48HfwG6x6ce</recordid><startdate>20120907</startdate><enddate>20120907</enddate><creator>Lane, Timothy K</creator><creator>D’Souza, Brendan R</creator><creator>Louie, Janis</creator><general>American Chemical Society</general><scope>IQODW</scope><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>7S9</scope><scope>L.6</scope><scope>5PM</scope></search><sort><creationdate>20120907</creationdate><title>Iron-Catalyzed Formation of 2‑Aminopyridines from Diynes and Cyanamides</title><author>Lane, Timothy K ; D’Souza, Brendan R ; Louie, Janis</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a534t-c2260ef058c35401fad456f65e1a5a0caedc320fc9c162dad1ebc2efb195fed23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>alkynes</topic><topic>Aminopyridines - chemical synthesis</topic><topic>Aminopyridines - chemistry</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Cyanamide - chemistry</topic><topic>cyanamides</topic><topic>Cyclization</topic><topic>Diynes - chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Iron - chemistry</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>pyridines</topic><topic>regioselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lane, Timothy K</creatorcontrib><creatorcontrib>D’Souza, Brendan R</creatorcontrib><creatorcontrib>Louie, Janis</creatorcontrib><collection>Pascal-Francis</collection><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>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lane, Timothy K</au><au>D’Souza, Brendan R</au><au>Louie, Janis</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Iron-Catalyzed Formation of 2‑Aminopyridines from Diynes and Cyanamides</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2012-09-07</date><risdate>2012</risdate><volume>77</volume><issue>17</issue><spage>7555</spage><epage>7563</epage><pages>7555-7563</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Diynes and cyanamides undergo an iron-catalyzed [2 + 2 + 2] cycloaddition to form highly substituted 2-aminopyridines in an atom-efficient manner that is both high yielding and regioselective. This system was also used to cyclize two terminal alkynes and a cyanamide to afford a 2,4,6-trisubstituted pyridine product regioselectively.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>22845666</pmid><doi>10.1021/jo3012418</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2012-09, Vol.77 (17), p.7555-7563 |
| issn | 0022-3263 1520-6904 1520-6904 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3480319 |
| source | ACS Publications; MEDLINE |
| subjects | alkynes Aminopyridines - chemical synthesis Aminopyridines - chemistry Catalysis Chemistry Cyanamide - chemistry cyanamides Cyclization Diynes - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Iron - chemistry Molecular Structure Organic chemistry Preparations and properties pyridines regioselectivity |
| title | Iron-Catalyzed Formation of 2‑Aminopyridines from Diynes and Cyanamides |
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