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Volumn 10, Issue 13, 2008, Pages 2621-2624

Diversity synthesis of complex pyridines yields a probe of a neurotrophic signaling pathway

Author keywords

[No Author keywords available]

Indexed keywords

NITRILE; PYRIDINE DERIVATIVE;

EID: 51649095908     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8004936     Document Type: Article
Times cited : (44)

References (40)
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    • Recent examples: (a) Doszczak, L.; Fey, P.; Tacke, R. Synlett 2007, 75, 3-756.
    • Recent examples: (a) Doszczak, L.; Fey, P.; Tacke, R. Synlett 2007, 75, 3-756.
  • 10
    • 33947147688 scopus 로고    scopus 로고
    • Additional examples are available in supporting information, 2007
    • (e) Kase, K.; Goswami, A.; Ohtaki, K.; Tanabe, E.; Saino, N.; Okamoto, S. Org. Lett. 2007, 9, 931-934. Additional examples are available in supporting information (2004-2006)
    • (2004) Org. Lett , vol.9 , pp. 931-934
    • Kase, K.1    Goswami, A.2    Ohtaki, K.3    Tanabe, E.4    Saino, N.5    Okamoto, S.6
  • 21
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    • A reaction of diynes with cyanamides using 2 in 1,4-dioxanes has been reported: Boñaga, L. V. R.; Zhang, H-C.; Maryanoff, B. E. Chem. Commun. 2004, 21, 2394-2395.
    • A reaction of diynes with cyanamides using 2 in 1,4-dioxanes has been reported: Boñaga, L. V. R.; Zhang, H-C.; Maryanoff, B. E. Chem. Commun. 2004, 21, 2394-2395.
  • 23
    • 0034826606 scopus 로고    scopus 로고
    • In other intramolecular reactions, the length of the tether affects the regioselectivity; see: Moretto, A. F, Zhang, H-C, Maryanoff, B. E. J. Am. Chem. Soc. 2001, 123, 3157-3158
    • In other intramolecular reactions, the length of the tether affects the regioselectivity; see: Moretto, A. F.; Zhang, H-C.; Maryanoff, B. E. J. Am. Chem. Soc. 2001, 123, 3157-3158.
  • 24
    • 17144426927 scopus 로고    scopus 로고
    • Examples often append the silyl group externally: (a) McCormick, M. M.; Duong, H. A.; Zuo, G.; Louie, J. J. Am. Chem. Soc. 2005, 127, 5030-5031.
    • Examples often append the silyl group externally: (a) McCormick, M. M.; Duong, H. A.; Zuo, G.; Louie, J. J. Am. Chem. Soc. 2005, 127, 5030-5031.
  • 27
    • 27744501828 scopus 로고    scopus 로고
    • Coordination of pyridines with CpCo is also possible. Examples of coordination to products of [2 + 2 + 2]-cycloaddition exist. See: Gandon, V.; Leboeuf, D.; Amslinger, S.; Vollhardt, K. P. C.; Malacria, M.; Aubert, C. Angew. Chem., Int. Ed. 2005, 44, 7114-7118.
    • Coordination of pyridines with CpCo is also possible. Examples of coordination to products of [2 + 2 + 2]-cycloaddition exist. See: Gandon, V.; Leboeuf, D.; Amslinger, S.; Vollhardt, K. P. C.; Malacria, M.; Aubert, C. Angew. Chem., Int. Ed. 2005, 44, 7114-7118.
  • 31
    • 0037176243 scopus 로고    scopus 로고
    • For a [2 + 2 + 2] example with CO2, see: Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N. J. Am. Chem. Soc. 2002, 124, 15188-15189.
    • For a [2 + 2 + 2] example with CO2, see: Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N. J. Am. Chem. Soc. 2002, 124, 15188-15189.
  • 32
    • 0000110406 scopus 로고    scopus 로고
    • Diyne cycloaddition with isocyanates: Yamamoto, Y.; Takagishi, H.; Itoh, K. Org. Lett. 2001, 3, 2117-2119.
    • (b) Diyne cycloaddition with isocyanates: Yamamoto, Y.; Takagishi, H.; Itoh, K. Org. Lett. 2001, 3, 2117-2119.
  • 33
    • 36649005330 scopus 로고    scopus 로고
    • For the synthesis of a collection of diverse silylated diynes, see
    • For the synthesis of a collection of diverse silylated diynes, see: Gray, B. L.; Schreiber, S. L. J. Comb. Chem. 2007, 9, 1028-1035.
    • (2007) J. Comb. Chem , vol.9 , pp. 1028-1035
    • Gray, B.L.1    Schreiber, S.L.2
  • 36
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    • The EGF domain of Neuregulin 1β1 (corresponding to amino acid residues 176-246 of heregulin-1β1), was expressed and purified from E. coli (R&D Systems; no. 396-HB) and reconstituted in phosphate-buffered saline (PBS) with 0.1% bovine serum albumin as a nonspecific carrier and frozen in aliquots at -20°C.
    • The EGF domain of Neuregulin 1β1 (corresponding to amino acid residues 176-246 of heregulin-1β1), was expressed and purified from E. coli (R&D Systems; no. 396-HB) and reconstituted in phosphate-buffered saline (PBS) with 0.1% bovine serum albumin as a nonspecific carrier and frozen in aliquots at -20°C.
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    • Manuscript in preparation
    • Kuai, L. et al. Manuscript in preparation.
    • Kuai, L.1
  • 40
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    • Procedure for pyridine synthesis: Diisopropyl(pent-1-yn-3-yloxy, phenylethynyl)silane 1 (10.0 mg, 0.033 mmol) was placed into an oven-dried sealed tube and dissolved in degassed THF (0.67 mL, Nitriles 7-18 (0.05 mmol, 1.5 equiv) were added to the stirring solution. After complete dissolution, a solution of cyclopentadienylcobalt(I) dicarbonyl (1.8 mg, 0.010 mmol, 30 mol , in degassed xylenes (50 μL) was introduced by syringe, giving a pale yellow solution that was submerged into an oil bath preheated to 140°C. After 24 h, the dark brown solution was cooled to ambient temperature and loaded onto a 4 g silica plug. Filtration was performed using an Isco Combiflash system using a gradient solvent commencing with hexanes and ending with 1/1 hexanes/ethyl acetate total of approximately 40 mL, which effectively removed insoluble cobalt byproducts. Pooled fractions were concentrated in vacuo and assayed for conversion by 1H NMR. Purification was pe
    • 1H NMR. Purification was performed by silica gel chromatography using an Isco Combiflash 12 g column with 20:1 hexanes/EtOAc as eluant, providing the corresponding pyridines 19-26.


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