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Volumn 131, Issue 8, 2009, Pages 3042-3048

C-H bonds as ubiquitous functionality: A general approach to complex arylated pyrazoles via sequential regioselective C-arylation and N-alkylation enabled by SEM-group transposition

Author keywords

[No Author keywords available]

Indexed keywords

ARENE RINGS; ARYLATIONS; C-H BOND; CATALYTIC SYSTEM; GENERAL APPROACH; HETEROARENES; N-ALKYLATION; NEW APPROACHES; ONE STEP; PROTECTING GROUP; PROTEIN LIGANDS; PYRAZOLES; REGIO-SELECTIVE; REGIOCONTROL; SEM; SUZUKI COUPLINGS; SYNTHETIC METHODS;

EID: 67749101415     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8096114     Document Type: Article
Times cited : (182)

References (54)
  • 2
    • 0003607021 scopus 로고    scopus 로고
    • Katrizky, A. R, Rees, C. W, Scriven, E. F. V, Eds, Pergamon: Oxford
    • (a) Elguero, J. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996, Vol 5.
    • (1996) Comprehensive Heterocyclic Chemistry , vol.5
    • Elguero, J.1
  • 3
    • 85041944712 scopus 로고    scopus 로고
    • Pyrazoles as Drugs: Facts and Fantasies
    • Attanasi, O. A, Spinelli, D, Eds, Italian Society of Chemistry: Roma
    • (b) Elguero, J.; Goya, P.; Jagerovic, N.; Silva, A. M. S. Pyrazoles as Drugs: Facts and Fantasies. In Targets in Heterocyclic Systems; Attanasi, O. A., Spinelli, D., Eds.; Italian Society of Chemistry: Roma, 2002; Vol. 6, pp 52-98.
    • (2002) Targets in Heterocyclic Systems , vol.6 , pp. 52-98
    • Elguero, J.1    Goya, P.2    Jagerovic, N.3    Silva, A.M.S.4
  • 8
    • 68049131916 scopus 로고    scopus 로고
    • Science of Synthesis; Stanovnik, B., Svete, J. D. Eds.; Thieme: Stuttgart, 2002; 12, pp 22-81, pp 84-91.
    • Science of Synthesis; Stanovnik, B., Svete, J. D. Eds.; Thieme: Stuttgart, 2002; Vol.'12, pp 22-81, pp 84-91.
  • 11
    • 45549094745 scopus 로고    scopus 로고
    • Deng, X.; Mani, N. S. Org. Lett. 2008, 10, 13071310.
    • (c) Deng, X.; Mani, N. S. Org. Lett. 2008, 10, 13071310.
  • 14
    • 44949111442 scopus 로고    scopus 로고
    • As recently reported, THP protecting group and its transposition has been used to achieve pyrazole lithiation and regioselective preparation of N-THP-pyrazolylboronate esters. McLaughlin, M.; Marcantonio, K.; Chen, C.-y.; Davies, I. W. J. Org. Chem. 2008, 73, 4309-1312.
    • As recently reported, THP protecting group and its transposition has been used to achieve pyrazole lithiation and regioselective preparation of N-THP-pyrazolylboronate esters. McLaughlin, M.; Marcantonio, K.; Chen, C.-y.; Davies, I. W. J. Org. Chem. 2008, 73, 4309-1312.
  • 16
    • 20444370318 scopus 로고    scopus 로고
    • Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 80508057.
    • (b) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 80508057.
  • 19
    • 68049131912 scopus 로고    scopus 로고
    • Wang. X.; Lane, B. S.; Sames. D. J. Am. Chem. Soc. 2005, 127, 49964997.
    • Wang. X.; Lane, B. S.; Sames. D. J. Am. Chem. Soc. 2005, 127, 49964997.
  • 20
    • 34248361209 scopus 로고    scopus 로고
    • The development of catalytic methods for C-H arylation of arenes and heteroarenes is an active area of research. For recent reviews, see: (a) Campeau, L.-C, Stuart, D. R, Fagnou, K. Aldrichimica Acta 2007, 40, 35-41
    • The development of catalytic methods for C-H arylation of arenes and heteroarenes is an active area of research. For recent reviews, see: (a) Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichimica Acta 2007, 40, 35-41.
  • 22
    • 34250655628 scopus 로고    scopus 로고
    • Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 11731193.
    • (c) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 11731193.
  • 24
    • 28244474558 scopus 로고    scopus 로고
    • Recent examples of azole C-aryration reported by others. (a) Bowie, A. L.; Hughes, C. C.; Trauner, D. Org. Lett. 2005, 7, 5207-5209.
    • Recent examples of azole C-aryration reported by others. (a) Bowie, A. L.; Hughes, C. C.; Trauner, D. Org. Lett. 2005, 7, 5207-5209.
  • 27
    • 33745656245 scopus 로고    scopus 로고
    • Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2006, 45, 15891591.
    • (d) Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2006, 45, 15891591.
  • 33
    • 33744733072 scopus 로고    scopus 로고
    • Intramolecular C-arylation of pyrazoles have been reported via an alkylation/arylation sequence. Blaszykowski, C.; Aktoudianakis, E.; Bressy, C.; Álberico, D.; Lautens, M. Org. Lett. 2006, 8, 2043-2045.
    • Intramolecular C-arylation of pyrazoles have been reported via an alkylation/arylation sequence. Blaszykowski, C.; Aktoudianakis, E.; Bressy, C.; Álberico, D.; Lautens, M. Org. Lett. 2006, 8, 2043-2045.
  • 34
    • 0001319197 scopus 로고    scopus 로고
    • The SEM group is also a directing group for lithiation of azoles including pyrazoles. (a) Edwards, M. P.; Doherty, A. M.; Lev, S. V.; Organ. H. M. Tetrahedron 1986, 42, 3723-3729.
    • The SEM group is also a directing group for lithiation of azoles including pyrazoles. (a) Edwards, M. P.; Doherty, A. M.; Lev, S. V.; Organ. H. M. Tetrahedron 1986, 42, 3723-3729.
  • 39
    • 68049123857 scopus 로고    scopus 로고
    • Science of Synthesis; Stanovnik. B.. Svete. J. D., Eds.; Thieme: Stuttgart, 2002; 12, pp 173-203.
    • (a) Science of Synthesis; Stanovnik. B.. Svete. J. D., Eds.; Thieme: Stuttgart, 2002; Vol. 12, pp 173-203.
  • 41
    • 0001029289 scopus 로고
    • Pyrazoles, pyrazolines, pyrazolidines, indazoles, and condensed rings
    • Wiley. R. H, Ed, Interscience Publishers: New York
    • (c) Behr, L. C.; Fusco, R.; Jarboe, C. H. Pyrazoles, pyrazolines, pyrazolidines, indazoles, and condensed rings. In The Chemistry of Heterocyclic Compounds; Wiley. R. H., Ed.; Interscience Publishers: New York, 1967; Vol. 22 pp 107-109.
    • (1967) The Chemistry of Heterocyclic Compounds , vol.22 , pp. 107-109
    • Behr, L.C.1    Fusco, R.2    Jarboe, C.H.3
  • 43
    • 31944442069 scopus 로고    scopus 로고
    • The palladium-carbonate system also showed preference for acidic C-H bonds: Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc 2006, 728, 1066-1067.
    • The palladium-carbonate system also showed preference for acidic C-H bonds: Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc 2006, 728, 1066-1067.
  • 46
    • 68049131914 scopus 로고    scopus 로고
    • Luo. G.; Chen. L.; Dubowchik, G. J. Org. Chem. 2006, 7/. 53925395.
    • Luo. G.; Chen. L.; Dubowchik, G. J. Org. Chem. 2006, 7/. 53925395.


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