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Volumn 8, Issue 25, 2006, Pages 5789-5792

Isocyanide addition to pyridinium salts. Efficient entry into substituted nicotinonitrile derivatives

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CYANIDE; NICOTINAMIDE; NICOTINIC ACID DERIVATIVE; NITRILE; PYRIDINIUM DERIVATIVE; QUINOLINE DERIVATIVE;

EID: 33846314722     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062327w     Document Type: Article
Times cited : (30)

References (35)
  • 1
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    • Product Class 1: Pyridines
    • Black, D. StC, Ed, Thieme Verlag: Stuttgart
    • Spitzner, D. Product Class 1: Pyridines. In Science of Synthesis; Black, D. StC., Ed.; Thieme Verlag: Stuttgart, 2005; Vol. 15, pp 11-284.
    • (2005) Science of Synthesis , vol.15 , pp. 11-284
    • Spitzner, D.1
  • 8
    • 84890597202 scopus 로고    scopus 로고
    • For an overview, see:, Zhu, J, Bienaymé, H, Eds, Wiley-WCH: Weinheim
    • (c) For an overview, see: Multicomponent Reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-WCH: Weinheim, 2005.
    • (2005) Multicomponent Reactions
  • 10
    • 28844455328 scopus 로고    scopus 로고
    • For additions to N-triflylpyridinium salts, see
    • (b) For additions to N-triflylpyridinium salts, see: Corey, E. J.; Tian, Y. Org. Lett. 2005, 7, 5535.
    • (2005) Org. Lett , vol.7 , pp. 5535
    • Corey, E.J.1    Tian, Y.2
  • 12
    • 4644272647 scopus 로고    scopus 로고
    • Pyridines only react in Reissert processes under special conditions. See:, and references therein
    • Pyridines only react in Reissert processes under special conditions. See: Ichikawa, E.; Suzuki, M.; Yabu, K.; Albert, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 11808 and references therein.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 11808
    • Ichikawa, E.1    Suzuki, M.2    Yabu, K.3    Albert, M.4    Kanai, M.5    Shibasaki, M.6
  • 13
    • 14744290361 scopus 로고    scopus 로고
    • Recently, the reactivity of N-fluoropyridinium salts with isocyanides has been described: Kiselyov, A. S. Tetrahedron Lett. 2005, 46, 2279.
    • Recently, the reactivity of N-fluoropyridinium salts with isocyanides has been described: Kiselyov, A. S. Tetrahedron Lett. 2005, 46, 2279.
  • 16
    • 33748925555 scopus 로고    scopus 로고
    • and references therein
    • (c) Pirali, T.; Tron, G. C.; Zhu, J. Org. Lett. 2006, 8, 4145 and references therein.
    • (2006) Org. Lett , vol.8 , pp. 4145
    • Pirali, T.1    Tron, G.C.2    Zhu, J.3
  • 17
    • 33846313370 scopus 로고    scopus 로고
    • NAD; Chemistry and Its Role in Biology and Medicine. Pankiewicz, K. W., Ed.; In Curr. Med. Chem. 2004, 11 (7).
    • (a) NAD; Chemistry and Its Role in Biology and Medicine. Pankiewicz, K. W., Ed.; In Curr. Med. Chem. 2004, 11 (7).
  • 25
    • 0033551720 scopus 로고    scopus 로고
    • For different trappings, see
    • For different trappings, see: Livinghouse, T. Tetrahedron 1999, 55, 9947.
    • (1999) Tetrahedron , vol.55 , pp. 9947
    • Livinghouse, T.1
  • 26
    • 84982077736 scopus 로고
    • For a Ugi-type process upon a quinolininium salt, see
    • (a) For a Ugi-type process upon a quinolininium salt, see: Ugi, I.; Böttner, E. Liebigs Ann. Chem. 1963, 670, 74.
    • (1963) Liebigs Ann. Chem , vol.670 , pp. 74
    • Ugi, I.1    Böttner, E.2
  • 27
    • 33846314518 scopus 로고    scopus 로고
    • Also see ref 2a
    • (b) Also see ref 2a.
  • 30
    • 33846270871 scopus 로고    scopus 로고
    • This may take place through the addition at the α′ position of the isoquinoline ring, to generate an o-quinodimethane intermediate (attempts to trap such species by Diels-Alder reactions resulted in failure, which may rearrange (1,5-sigmatropic shift) to the final compound 5, although an intermolecular process cannot be ruled out. Another interesting possibility, suggested by a referee, involves the isocyanide addition to the áposition and the trapping of the nitrilium ion by the carboxamido group to yield a strained (but precedented) anti-Bredt intermediate, which would rearrange to 5
    • This may take place through the addition at the α′ position of the isoquinoline ring, to generate an o-quinodimethane intermediate (attempts to trap such species by Diels-Alder reactions resulted in failure), which may rearrange (1,5-sigmatropic shift) to the final compound 5, although an intermolecular process cannot be ruled out. Another interesting possibility, suggested by a referee, involves the isocyanide addition to the áposition and the trapping of the nitrilium ion by the carboxamido group to yield a strained (but precedented) anti-Bredt intermediate, which would rearrange to 5.
  • 34
    • 33846286279 scopus 로고    scopus 로고
    • More than 75,800 substances with the nicotinonitrile core are listed in SciFinder (2006), most of them in biomedical patents.
    • (a) More than 75,800 substances with the nicotinonitrile core are listed in SciFinder (2006), most of them in biomedical patents.
  • 35
    • 31444455643 scopus 로고    scopus 로고
    • Interestingly the cyano substituent is the synthetic precursor for the tetrazole moiety. For a recent result, see
    • (b) Interestingly the cyano substituent is the synthetic precursor for the tetrazole moiety. For a recent result, see: Lukyanov, S. M.; Bliznets, I. V.; Shorshnev, S. V.; Aleksandrov, G. G.; Stepanov, A. E.; Vasil'ev, A. A. Tetrahedron 2006, 62, 1849.
    • (2006) Tetrahedron , vol.62 , pp. 1849
    • Lukyanov, S.M.1    Bliznets, I.V.2    Shorshnev, S.V.3    Aleksandrov, G.G.4    Stepanov, A.E.5    Vasil'ev, A.A.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.