메뉴 건너뛰기




Volumn , Issue 5, 2009, Pages 721-730

Synthesis of 5,7-dichloro-6-azaindoles and functionalization via a highly selective lithium-chlorine exchange

Author keywords

Azaindole; Fischer cyclizations; Meta lations; Palladium; Pyrrolopyridine

Indexed keywords

AZAINDOLE; AZAINDOLES; FISCHER CYCLIZATIONS; FUNCTIONALIZATION; META-LATIONS; PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS; PYRROLOPYRIDINE;

EID: 63449098374     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1083354     Document Type: Article
Times cited : (9)

References (41)
  • 1
    • 33847345910 scopus 로고    scopus 로고
    • For leading references to the physiological activity of indole derivatives, see: (a) Sturino, C. F.; O'Neill, G. P.; Lachance, N.; Boyd, M. J.; Berthelette, C.; Labelle, M.; Li, L. H.; Roy, B.; Scheigetz, J.; Tsou, N. N.; Bateman, K. P.; Day, S. H.; Levesque, J. F.; Seto, C.; Silva, J. M.; Carriere, M.; Denis, D.; Greig, G. M.; Kargman, S. L.; Lamontagne, S.; Mathieu, M.; Sawyer, N.; Slipetz, D. M.; Jones, T. R.; Mcauliffe, M.; Piechuta, H.; Nicoll-Griffith, D. A.; Wang, Z.; Zamboni, R. J.; Young, R. N.; Metters, K. M. J. Med. Chem. 2007, 50, 794.
    • For leading references to the physiological activity of indole derivatives, see: (a) Sturino, C. F.; O'Neill, G. P.; Lachance, N.; Boyd, M. J.; Berthelette, C.; Labelle, M.; Li, L. H.; Roy, B.; Scheigetz, J.; Tsou, N. N.; Bateman, K. P.; Day, S. H.; Levesque, J. F.; Seto, C.; Silva, J. M.; Carriere, M.; Denis, D.; Greig, G. M.; Kargman, S. L.; Lamontagne, S.; Mathieu, M.; Sawyer, N.; Slipetz, D. M.; Jones, T. R.; Mcauliffe, M.; Piechuta, H.; Nicoll-Griffith, D. A.; Wang, Z.; Zamboni, R. J.; Young, R. N.; Metters, K. M. J. Med. Chem. 2007, 50, 794.
  • 4
    • 0034615797 scopus 로고    scopus 로고
    • and references therein. For review on indoles synthesis, see
    • For review on indoles synthesis, see: Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045; and references therein.
    • (2000) J. Chem. Soc., Perkin Trans. 1 , vol.1045
    • Gribble, G.W.1
  • 5
    • 33746864043 scopus 로고    scopus 로고
    • and references therein. For recent reviews on palladium-catalyzed synthesis of indoles, see: a
    • For recent reviews on palladium-catalyzed synthesis of indoles, see: (a) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875; and references therein.
    • (2006) Chem. Rev , vol.106 , pp. 2875
    • Humphrey, G.R.1    Kuethe, J.T.2
  • 6
    • 22944454156 scopus 로고    scopus 로고
    • and references therein
    • (b) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873; and references therein.
    • (2005) Chem. Rev , vol.105 , pp. 2873
    • Cacchi, S.1    Fabrizi, G.2
  • 10
    • 34547134215 scopus 로고    scopus 로고
    • For reviews on azaindoles synthesis, see: a
    • For reviews on azaindoles synthesis, see: (a) Popowycz, F.; Merour, J.-Y.; Joseph, B. Tetrahedron 2007, 63, 8689.
    • (2007) Tetrahedron , vol.63 , pp. 8689
    • Popowycz, F.1    Merour, J.-Y.2    Joseph, B.3
  • 24
    • 63449127916 scopus 로고    scopus 로고
    • The use of a condenser is not recommended
    • The use of a condenser is not recommended.
  • 25
    • 63449102820 scopus 로고    scopus 로고
    • Typically, aminopyridine 1 was isolated in less than 5
    • Typically, aminopyridine 1 was isolated in less than 5%.
  • 27
    • 0038644233 scopus 로고    scopus 로고
    • For selective lithium-bromine exchange on indoles, see: a
    • For selective lithium-bromine exchange on indoles, see: (a) Li, L.; Martins, A. Tetrahedron Lett. 2003, 44, 5987.
    • (2003) Tetrahedron Lett , vol.44 , pp. 5987
    • Li, L.1    Martins, A.2
  • 34
    • 8644283612 scopus 로고    scopus 로고
    • For leading references on ortho-lithiation of halogenated pyridines, see: a
    • For leading references on ortho-lithiation of halogenated pyridines, see: (a) Pierrat, P.; Gros, P.; Fort, Y. Synlett 2004, 2319.
    • (2004) Synlett , pp. 2319
    • Pierrat, P.1    Gros, P.2    Fort, Y.3
  • 37
    • 0035821359 scopus 로고    scopus 로고
    • and references therein. Review
    • (d) Review: Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4059; and references therein.
    • (2001) Tetrahedron , vol.57 , pp. 4059
    • Mongin, F.1    Quéguiner, G.2
  • 40
    • 63449100545 scopus 로고    scopus 로고
    • 1H NMR of the unpurified reaction mixture.
    • 1H NMR of the unpurified reaction mixture.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.