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Volumn 15, Issue 9, 2009, Pages 2129-2139

Synthesis of tricyclic fused 3-aminopyridines through intramolecular Coi-catalyzed [2+2+2] cycloaddition between ynamides, nitriles, and alkynes

Author keywords

Alkynes; Cobalt; Cycloaddition; Hiyama cross coupling; Pyridine

Indexed keywords

ACETYLENE; AMINES; COBALT; CYANIDES; SILANES;

EID: 60749134158     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802301     Document Type: Article
Times cited : (78)

References (68)
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    • For reviews on [2,+2,+2] cycloaddition reactions, see: a K. P. C. Vollhardt, Angew. Chem. 1984, 96, 525;
    • For reviews on [2,+2,+2] cycloaddition reactions, see: a) K. P. C. Vollhardt, Angew. Chem. 1984, 96, 525;
  • 23
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    • For [2,+2,+2] cocyclizations between an. ynamide and two alkynes to give benzenamines, see: a B. Witulski, T. Stengel, Angew. Chem. 1999, 111, 2521;
    • For [2,+2,+2] cocyclizations between an. ynamide and two alkynes to give benzenamines, see: a) B. Witulski, T. Stengel, Angew. Chem. 1999, 111, 2521;
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    • For recent examples of bimolecular and intramolecular [2,+2,+ 2] cocyclization of nitriles to diynes, see, respectively: a D. D. Young, A. Deiters, Angew. Chem. 2007, 119, 5279;
    • For recent examples of bimolecular and intramolecular [2,+2,+ 2] cocyclization of nitriles to diynes, see, respectively: a) D. D. Young, A. Deiters, Angew. Chem. 2007, 119, 5279;
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    • This step proved more difficult than expected using standard conditions, thus we had to use an alternate method, see: E. Kaiser, Sr, J. P. Tam, T. M. Kubiak, R. B. Merrifield, Tetrahedron Lett. 1988, 29, 303
    • This step proved more difficult than expected using standard conditions, thus we had to use an alternate method, see: E. Kaiser, Sr., J. P. Tam, T. M. Kubiak, R. B. Merrifield, Tetrahedron Lett. 1988, 29, 303.
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    • Azeto[2,3-c]pyridine-2(1H)-one as been detected below 0C, see: C. Wen trup, G. Gross, Angew. Chem. 1983, 95, 552;
    • Azeto[2,3-c]pyridine-2(1H)-one as been detected below 0C, see: C. Wen trup, G. Gross, Angew. Chem. 1983, 95, 552;
  • 56
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    • As method A is more convenient to carry out, method B was not performed any longer. From the first three examples, it seems clear that both catalysts give similar results
    • As method A is more convenient to carry out, method B was not performed any longer. From the first three examples, it seems clear that both catalysts give similar results.
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    • 60749110802 scopus 로고    scopus 로고
    • For reviews of the Hiyama reaction, see, for example: a S. E. Denmark, R. F. Sweis in Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004, Chapter 4;
    • For reviews of the Hiyama reaction, see, for example: a) S. E. Denmark, R. F. Sweis in Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004, Chapter 4;
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    • See: for Hiyama cross-coupling of chloro-, fluoro-, and methoxypyridyltrimethylsilanes: a P. Pierrat, P. Gros, Y. Fort, Org. Lett. 2005, 7, 697; for cross-couplings of (2-pyridyl)allyldimethylsilanes with aryliodides, see:
    • See: for Hiyama cross-coupling of chloro-, fluoro-, and methoxypyridyltrimethylsilanes: a) P. Pierrat, P. Gros, Y. Fort, Org. Lett. 2005, 7, 697; for cross-couplings of (2-pyridyl)allyldimethylsilanes with aryliodides, see:
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    • for phosphazene base-promoted functionalization of pyridyltrimethylsilanes
    • b) T. Nokami, Y. Tomida, T. Kamei, K. Itami, J.-i. Yoshida. Org. Lett. 2006, 8, 729; for phosphazene base-promoted functionalization of pyridyltrimethylsilanes:
    • (2006) Org. Lett , vol.8 , pp. 729
    • Nokami, T.1    Tomida, Y.2    Kamei, T.3    Itami, K.4    Yoshida, J.-I.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.