CpRuCl-Catalyzed [2 + 2 + 2] Cycloadditions of α,ω-Diynes with Electron-Deficient Carbon−Heteroatom Multiple Bonds Leading to Heterocycles
In the presence of a catalytic amount of Cp*RuCl(cod), 1,6-diynes were allowed to react chemo- and regioselectively with electron-deficient nitriles and heterocumulenes at 60−90 °C to afford heterocyclic compounds. The mechanism of the ruthenium-catalyzed regioselective formations of bicyclic pyridi...
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| Veröffentlicht in: | Journal of the American Chemical Society 2005-01, Vol.127 (2), p.605-613 |
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| container_title | Journal of the American Chemical Society |
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| creator | Yamamoto, Yoshihiko Kinpara, Keisuke Saigoku, Tomoaki Takagishi, Hideyuki Okuda, Satoshi Nishiyama, Hisao Itoh, Kenji |
| description | In the presence of a catalytic amount of Cp*RuCl(cod), 1,6-diynes were allowed to react chemo- and regioselectively with electron-deficient nitriles and heterocumulenes at 60−90 °C to afford heterocyclic compounds. The mechanism of the ruthenium-catalyzed regioselective formations of bicyclic pyridines and pyridones were analyzed on the basis of density functional calculations. Cyclocotrimerizations of ethyl propiolate with ethyl cyanoformate or propyl isocyanate gave rise to two of the four possible pyridine or pyridone regioisomers. |
| doi_str_mv | 10.1021/ja045694g |
| format | Article |
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The mechanism of the ruthenium-catalyzed regioselective formations of bicyclic pyridines and pyridones were analyzed on the basis of density functional calculations. 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Am. Chem. Soc</addtitle><description>In the presence of a catalytic amount of Cp*RuCl(cod), 1,6-diynes were allowed to react chemo- and regioselectively with electron-deficient nitriles and heterocumulenes at 60−90 °C to afford heterocyclic compounds. The mechanism of the ruthenium-catalyzed regioselective formations of bicyclic pyridines and pyridones were analyzed on the basis of density functional calculations. 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Am. Chem. Soc</addtitle><date>2005-01-19</date><risdate>2005</risdate><volume>127</volume><issue>2</issue><spage>605</spage><epage>613</epage><pages>605-613</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>In the presence of a catalytic amount of Cp*RuCl(cod), 1,6-diynes were allowed to react chemo- and regioselectively with electron-deficient nitriles and heterocumulenes at 60−90 °C to afford heterocyclic compounds. The mechanism of the ruthenium-catalyzed regioselective formations of bicyclic pyridines and pyridones were analyzed on the basis of density functional calculations. Cyclocotrimerizations of ethyl propiolate with ethyl cyanoformate or propyl isocyanate gave rise to two of the four possible pyridine or pyridone regioisomers.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15643884</pmid><doi>10.1021/ja045694g</doi><tpages>9</tpages></addata></record> |
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| source | ACS Publications |
| subjects | Chemistry Exact sciences and technology Kinetics and mechanisms Organic chemistry Reactivity and mechanisms |
| title | CpRuCl-Catalyzed [2 + 2 + 2] Cycloadditions of α,ω-Diynes with Electron-Deficient Carbon−Heteroatom Multiple Bonds Leading to Heterocycles |
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