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Volumn 79, Issue 19, 2014, Pages 9094-9103

C-H activation guided by aromatic N-H ketimines: Synthesis of functionalized isoquinolines using benzyl azides and alkynes

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; AROMATIZATION; CATALYSIS; ETHERS; NITROGEN COMPOUNDS;

EID: 84907779758     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501465q     Document Type: Article
Times cited : (67)

References (82)
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    • A conventional method for the synthesis of N-H ketimines is the reaction of organic nitriles with alkyl lithium or Gregnard reagents, followed by protonation with methanol; see: Chen, G.-M.; Brown, H. C. J. Am. Chem. Soc. 2000, 122, 4217-4218
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  • 29
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    • The hydrochloride salts of N-H ketimines can be isolated and used for the enantioselective hydrogenation to give the corresponding chiral amines
    • The hydrochloride salts of N-H ketimines can be isolated and used for the enantioselective hydrogenation to give the corresponding chiral amines: Hou, G.; Gosselin, F.; Li, W.; McWilliams, J. C.; Sun, Y.; Weisel, M.; O'Shea, P. D.; Chen, C.-Y.; Davies, I. W.; Zhang, X. J. Am. Chem. Soc. 2009, 131, 9882-9883
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 9882-9883
    • Hou, G.1    Gosselin, F.2    Li, W.3    McWilliams, J.C.4    Sun, Y.5    Weisel, M.6    O'Shea, P.D.7    Chen, C.-Y.8    Davies, I.W.9    Zhang, X.10
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    • US Patent 2612503-19520930.
    • Ullyot, G. E. US Patent 2612503-19520930, 1952.
    • (1952)
    • Ullyot, G.E.1
  • 50
    • 0012477017 scopus 로고    scopus 로고
    • A ruthenium acetate or a ruthenium chloride species would be formed, which is not active for the transformation of alkyl azides into the corresponding imines. For the formation of ruthenium triflate in the reaction using AgOTf, see: Casey, C. P.; Vos, T. E.; Singer, S. W.; Guzei, I. A. Organometallics 2002, 21, 5038-5046
    • (2002) Organometallics , vol.21 , pp. 5038-5046
    • Casey, C.P.1    Vos, T.E.2    Singer, S.W.3    Guzei, I.A.4
  • 58
    • 67449127136 scopus 로고    scopus 로고
    • For the steric effect in the regioselective C-H activation by Rh-catalyst, see: Li, L.; Brennessel, W. W.; Jones, W. D. Organometallics 2009, 28, 3492-3500
    • (2009) Organometallics , vol.28 , pp. 3492-3500
    • Li, L.1    Brennessel, W.W.2    Jones, W.D.3
  • 63
    • 12944323150 scopus 로고    scopus 로고
    • The formation of the imidate was further confirmed by the subsequent reaction with HCl to give its imidate salt. See: Yadav, V. K.; Babu, K. G. Eur. J. Org. Chem. 2005, 452-456
    • (2005) Eur. J. Org. Chem. , pp. 452-456
    • Yadav, V.K.1    Babu, K.G.2
  • 64
    • 84865744983 scopus 로고    scopus 로고
    • N -substituted benzimidates have been used in the Rh(III)-catalyzed synthesis of phthalides by cascade addition and cyclization with aldehydes; see: Lian, Y.; Bergman, R. G.; Ellman, J. A. Chem. Sci. 2012, 3, 3088-3092
    • (2012) Chem. Sci. , vol.3 , pp. 3088-3092
    • Lian, Y.1    Bergman, R.G.2    Ellman, J.A.3
  • 65
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    • Very recently, Glorius and co-workers have reported the synthesis of 1 H -indazoles, where simple imidates such as methyl- and ethyl benzimidate were employed in the RhIII/CuII-cocatalyzed reaction with tosyl azide; see: Yu, D.-G.; Suri, M.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 8802-8805
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 8802-8805
    • Yu, D.-G.1    Suri, M.2    Glorius, F.3
  • 66
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    • Recently, Jeganmohan and co-workers have reported the ruthenium-catalyzed aerobic oxidative cyclization of aromatic and heteroaromatic nitriles with alkynes to give isoquinolones; see: Reddy, M. C.; Manikandan, R.; Jeganmohan, M. Chem. Commun. 2013, 49, 6060-6062
    • (2013) Chem. Commun. , vol.49 , pp. 6060-6062
    • Reddy, M.C.1    Manikandan, R.2    Jeganmohan, M.3
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    • CCDC 965136 (14) and 965137 (15) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


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