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Volumn 45, Issue 8, 2004, Pages 1721-1724

An efficient one-pot synthesis of annulated pyridines utilising a directed ortho-metallation/transmetallation approach

Author keywords

Aminopyridines; Directed ortho metallation; Ring annulation; Transmetallation

Indexed keywords

ALKANE; ALKYLATING AGENT; AMINOPYRIDINE DERIVATIVE; CHELATING AGENT; PYRIDINE DERIVATIVE;

EID: 0842326659     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.096     Document Type: Article
Times cited : (18)

References (31)
  • 17
    • 0002307974 scopus 로고
    • For general reviews on the directed ortho-metallation reaction, see:
    • For general reviews on the directed ortho-metallation reaction, see: Gschwend H.W., Rodriguez H.R. Org. React. 26:1979;1.
    • (1979) Org. React. , vol.26 , pp. 1
    • Gschwend, H.W.1    Rodriguez, H.R.2
  • 19
    • 0035821359 scopus 로고    scopus 로고
    • For more focussed reviews on the metallation of azines and diazines, see:
    • For more focussed reviews on the metallation of azines and diazines, see: Mongin F., Quéguiner G. Tetrahedron. 57:2001;4059.
    • (2001) Tetrahedron. , vol.57 , pp. 4059
    • Mongin, F.1    Quéguiner, G.2
  • 23
    • 0028081131 scopus 로고
    • Prepared via a modified literature method, see:
    • Prepared via a modified literature method, see: Kelly T.A., McNeil D.W. Tetrahedron Lett. 35:1994;9003.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 9003
    • Kelly, T.A.1    McNeil, D.W.2
  • 25
    • 85030907364 scopus 로고    scopus 로고
    • note
    • Cooling the dianion mixture to -78°C prior to alkylation is necessary to prevent the formation of a dimeric species analogous to compound 6.
  • 26
    • 0000885668 scopus 로고
    • The pivaloyl protecting group is equally effective in the alkylation step, but failed to give any of the cyclisation products on warming. Pivaloyl protected aminopyridines have been used in DoM reactions previously, see:
    • The pivaloyl protecting group is equally effective in the alkylation step, but failed to give any of the cyclisation products on warming. Pivaloyl protected aminopyridines have been used in DoM reactions previously, see: Turner J.A. J. Org. Chem. 48:1983;3401.
    • (1983) J. Org. Chem. , vol.48 , pp. 3401
    • Turner, J.A.1
  • 27
    • 85030892723 scopus 로고    scopus 로고
    • note
    • 2: C, 59.47; H, 6.77; N, 9.91; Cl, 12.54. Found: C, 59.57; H, 6.79; N, 9.85; Cl, 12.53.
  • 28
    • 0034644389 scopus 로고    scopus 로고
    • The role of additives and the directing group in DoM reactions is still the subject of intense research, see:
    • The role of additives and the directing group in DoM reactions is still the subject of intense research, see: Rutherford J.L., Hoffman D., Collum D.B. J. Am. Chem. Soc. 122:2000;8640.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8640
    • Rutherford, J.L.1    Hoffman, D.2    Collum, D.B.3
  • 30
    • 0035920730 scopus 로고    scopus 로고
    • For examples of DoM reactions followed by lithium-copper transmetallation, see:
    • For examples of DoM reactions followed by lithium-copper transmetallation, see: Kamila S., Chandrani M., De A. Tetrahedron Lett. 42:2001;5955.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5955
    • Kamila, S.1    Chandrani, M.2    De, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.