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Volumn 45, Issue 46, 2006, Pages 7803-7806

Synthesis of nitrogen heterocycles by the ring opening of pyridinium salts

Author keywords

Biaryls; Cyclization; Indoles; Nitrogen heterocycles; Pyridinium salts

Indexed keywords

BIOCHEMISTRY; MEDICINE; SALTS; SUBSTITUTION REACTIONS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 33845314337     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602996     Document Type: Article
Times cited : (67)

References (26)
  • 5
    • 28244457575 scopus 로고    scopus 로고
    • For selected examples of reactions that occur without ring opening, see the following leading references: a) D. L. Comins, J. J. Sahn, Org. Lett. 2005, 7, 5227-5228;
    • (2005) Org. Lett. , vol.7 , pp. 5227-5228
    • Comins, D.L.1    Sahn, J.J.2
  • 8
    • 33845319549 scopus 로고    scopus 로고
    • note
    • Please see the Supporting Information for plausible mechanisms for these transformations.
  • 9
    • 85069754511 scopus 로고
    • For reviews, please see : a) J. Becher, Synthesis 1980, 589-613;
    • (1980) Synthesis , pp. 589-613
    • Becher, J.1
  • 16
    • 0010653530 scopus 로고    scopus 로고
    • For a comprehensive review of methods for indole synthesis, see: J. A. Joule, Sci. Synth. 2001, 10, 361-652.
    • (2001) Sci. Synth. , vol.10 , pp. 361-652
    • Joule, J.A.1
  • 18
    • 31944441649 scopus 로고    scopus 로고
    • and references therein
    • b) D. F. Taber, W. Tian, J. Am. Chem. Soc. 2006, 128, 1058-1059, and references therein.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 1058-1059
    • Taber, D.F.1    Tian, W.2
  • 19
    • 17144421373 scopus 로고    scopus 로고
    • For a review, see: (Ed.: D. Astruc), Wiley-VCH, Weinheim, Please see the Supporting Information for experimental details
    • For a review, see: A. Suzuki in Modern Arene Chemistry (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2002, pp. 53-106. Please see the Supporting Information for experimental details.
    • (2002) Modern Arene Chemistry , pp. 53-106
    • Suzuki, A.1
  • 20
    • 33845286491 scopus 로고    scopus 로고
    • note
    • Typical activating agents include 2,4-dinitrochlorobenzene, cyanogen halides, and sulfur trioxide. See references [1] and [4a].
  • 21
    • 33845341064 scopus 로고    scopus 로고
    • note
    • The conversion of 9 into 10 could conceivably occur through an electrocyclic pathway or a simple ionic mechanism; either would be followed by simple alkene geometrical isomerizations.
  • 22
    • 27544485685 scopus 로고    scopus 로고
    • and references therein
    • Y. Huang, A. M. Walji, C. H. Larsen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 15 051-15 053, and references therein. Although we suspect that the reactivity of products of type 7 will almost certainly be different from regular α,β-unsaturated aldehydes owing to the conjugation of the indole nitrogen, the incorporation of an electron-withdrawing N-protecting group might result in reasonable reactivity in iminium-based asymmetric organocatalysis. For a relevant example, please see reference [12].
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 15051-15053
    • Huang, Y.1    Walji, A.M.2    Larsen, C.H.3    MacMillan, D.W.C.4
  • 23
    • 0242582464 scopus 로고    scopus 로고
    • An indole-3-propenal was used in an asymmetric organocatalytic Diels-Alder reaction in a synthesis of hapalindole Q: A. C. Kinsman, M. A. Kerr, J. Am. Chem. Soc. 2003, 125, 14 120-14 125.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 14120-14125
    • Kinsman, A.C.1    Kerr, M.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.