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Volumn 51, Issue 11, 2012, Pages 2722-2726

In situ anionic shielding for regioselective metalation: Directed peri and iterative metalation routes to polyfunctionalized 7-azaindoles

Author keywords

heterocycles; metalation; regioselectivity; structure elucidation; synthetic methods

Indexed keywords

AZAINDOLES; DIRECTED ORTHO METALATION; HETEROCYCLES; HETEROCYCLIC SYSTEMS; IN-SITU; METALATIONS; REGIO-SELECTIVE; REGIOSELECTIVE METALATION; STRUCTURE ELUCIDATION; SUZUKI COUPLINGS; SYNTHETIC METHODS; TETRAMETHYLETHYLENEDIAMINE; TRIMETHYLSILYL;

EID: 84858028779     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201108016     Document Type: Article
Times cited : (31)

References (61)
  • 1
    • 79951684766 scopus 로고    scopus 로고
    • While this historic peri-nomenclature pertains usually to 1,8-disubstituted naphthalenes, the analogous arrangement and similar distances, 1,8-H-H naphthalenes=2.44 Å; 3,4-H-H 7-azaindole=3.00 Å
    • While this historic peri-nomenclature pertains usually to 1,8-disubstituted naphthalenes (, P. Kilian, F. R. Knight, J. D. Woolins, Chem. Eur. J. 2011, 12, 2302), the analogous arrangement and similar distances, 1,8-H-H naphthalenes=2.44 Å; 3,4-H-H 7-azaindole=3.00 Å
    • (2011) Chem. Eur. J. , vol.12 , pp. 2302
    • Kilian, P.1    Knight, F.R.2    Woolins, J.D.3
  • 3
    • 18744384857 scopus 로고    scopus 로고
    • in ed., 2 (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim
    • nd ed., Vol. 2 (Eds.:, A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004, pp. 761-813
    • (2004) nd , pp. 761-813
    • Anctil, E.J.-G.1    Snieckus, V.2
  • 8
    • 0141713788 scopus 로고    scopus 로고
    • in (Ed.: D. Astruc), WileyVCH, New York, ; For recent work
    • C. G. Hartung, V. Snieckus, in Modern Arene Chemistry (Ed.:, D. Astruc,), WileyVCH, New York, 2002, pp. 330-367; For recent work
    • (2002) Modern Arene Chemistry , pp. 330-367
    • Hartung, C.G.1    Snieckus, V.2
  • 12
    • 84858060001 scopus 로고
    • Sc. Ph.D. thesis, University of Waterloo, ON, Canada
    • R. J. Mills, Sc. Ph.D. thesis, University of Waterloo, ON, Canada, 1984
    • (1984)
    • Mills, R.J.1
  • 13
    • 84858060003 scopus 로고    scopus 로고
    • MSc Thesis, Queen's University, Kingston ON, Canada
    • J.-A. Morin, MSc Thesis, Queen's University, Kingston ON, Canada, 2007.
    • (2007)
    • Morin, J.-A.1
  • 25
    • 77954889728 scopus 로고    scopus 로고
    • 7-Azaindoles are also useful in material science and coordination chemistry, see review.
    • 7-Azaindoles are also useful in material science and coordination chemistry, see review:, S.-B. Zhao, S. Wang, Chem. Soc. Rev. 2010, 39, 3142.
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 3142
    • Zhao, S.-B.1    Wang, S.2
  • 26
    • 0346025404 scopus 로고    scopus 로고
    • Direct pyridine ring chlorination of 7-azaindole N-oxide to give 4- and 6-chloro derivatives (Reissert-Henze type reaction)
    • Direct pyridine ring chlorination of 7-azaindole N-oxide to give 4- and 6-chloro derivatives (Reissert-Henze type reaction):, C. Thibault, A. L'Heureux, R. S. Bhide, R. Ruel, Org. Lett. 2003, 5, 5023
    • (2003) Org. Lett. , vol.5 , pp. 5023
    • Thibault, C.1    L'Heureux, A.2    Bhide, R.S.3    Ruel, R.4
  • 27
    • 64049088672 scopus 로고    scopus 로고
    • Transition metal catalyzed synthesis of substituted systems: C6 arylation
    • Transition metal catalyzed synthesis of substituted systems: C6 arylation:, M. P. Huestis, K. Fagnou, Org. Lett. 2009, 11, 1357
    • (2009) Org. Lett. , vol.11 , pp. 1357
    • Huestis, M.P.1    Fagnou, K.2
  • 47
    • 7244228083 scopus 로고    scopus 로고
    • For thorough studies of naphthamides exhibiting similar properties, see.
    • For thorough studies of naphthamides exhibiting similar properties, see:, J. Clayden, A. Lund, L. Vallverdu, M. Helliwell, Nature 2004, 431, 966.
    • (2004) Nature , vol.431 , pp. 966
    • Clayden, J.1    Lund, A.2    Vallverdu, L.3    Helliwell, M.4
  • 57
    • 84858068999 scopus 로고    scopus 로고
    • Ph.D. Thesis, Queen's University
    • Y. Zhao, Ph.D. Thesis, Queen's University, 2010
    • (2010)
    • Zhao, Y.1
  • 58
    • 4544294700 scopus 로고    scopus 로고
    • For Ni-catalyzed cleavage of sulfonamides, see
    • For Ni-catalyzed cleavage of sulfonamides, see, R. R. Milburn, V. Snieckus, Angew. Chem. 2004, 116, 910
    • (2004) Angew. Chem. , vol.116 , pp. 910
    • Milburn, R.R.1    Snieckus, V.2
  • 61
    • 84858069002 scopus 로고
    • tBuLi, often used for the C4 metalation of gramine, is a pyrophoric base
    • tBuLi, often used for the C4 metalation of gramine (, M. Iwao, Heterocycles 1993, 36, 19), is a pyrophoric base
    • (1993) Heterocycles , vol.36 , pp. 19
    • Iwao, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.