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Product Class 1: Pyridines
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Black, D. StC, Ed, Thieme Verlag: Stuttgart
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Spitzner, D. Product Class 1: Pyridines. In Science of Synthesis; Black, D. StC., Ed.; Thieme Verlag: Stuttgart, 2005; Vol. 15, pp 11-284.
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For an overview, see:, Zhu, J, Bienaymé, H, Eds, Wiley-WCH: Weinheim
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(c) For an overview, see: Multicomponent Reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-WCH: Weinheim, 2005.
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Multicomponent Reactions
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10
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28844455328
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For additions to N-triflylpyridinium salts, see
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(b) For additions to N-triflylpyridinium salts, see: Corey, E. J.; Tian, Y. Org. Lett. 2005, 7, 5535.
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Org. Lett
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Corey, E.J.1
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For instance, see
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For instance, see: Bunting, J. W.; Sindhuatmadja, S. J. Org. Chem. 1980, 45, 5411.
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Bunting, J.W.1
Sindhuatmadja, S.2
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12
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4644272647
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Pyridines only react in Reissert processes under special conditions. See:, and references therein
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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.
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J. Am. Chem. Soc
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Ichikawa, E.1
Suzuki, M.2
Yabu, K.3
Albert, M.4
Kanai, M.5
Shibasaki, M.6
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13
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Recently, the reactivity of N-fluoropyridinium salts with isocyanides has been described: Kiselyov, A. S. Tetrahedron Lett. 2005, 46, 2279.
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Recently, the reactivity of N-fluoropyridinium salts with isocyanides has been described: Kiselyov, A. S. Tetrahedron Lett. 2005, 46, 2279.
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14
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(a) Janvier, P.; Sun, X.; Bienaymé, H.; Zhu, J. J. Am. Chem. Soc. 2002, 124, 2560.
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and references therein
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(c) Pirali, T.; Tron, G. C.; Zhu, J. Org. Lett. 2006, 8, 4145 and references therein.
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Org. Lett
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NAD; Chemistry and Its Role in Biology and Medicine. Pankiewicz, K. W., Ed.; In Curr. Med. Chem. 2004, 11 (7).
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(a) NAD; Chemistry and Its Role in Biology and Medicine. Pankiewicz, K. W., Ed.; In Curr. Med. Chem. 2004, 11 (7).
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(b) Yang, J.; Klaidman, K.; Adams, J. D. Med. Chem. Rev. 2004, 1, 13.
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(c) Ogata, S.; Takeuchi, M.; Teradaira, S.; Yamamoto, N.; Iwata, K.; Okumura, K.; Taguchi, H. Biosci. Biotechnol. Biochem. 2002, 66, 641.
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Ogata, S.1
Takeuchi, M.2
Teradaira, S.3
Yamamoto, N.4
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Okumura, K.6
Taguchi, H.7
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(d) Girgis, A. S.; Hosni, H. M.; Barsoum, F. F. Bioorg. Med. Chem. 2006, 14, 4466.
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Girgis, A.S.1
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(e) Broussy, S.; Bernardes-Génisson, V.; Quémard, A.; Meunier, B.; Bernadou, J. J. Org. Chem. 2005, 70, 10502.
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Broussy, S.1
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Quémard, A.3
Meunier, B.4
Bernadou, J.5
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(f) Argyrou, A.; Vetting, M. W.; Aladegbami, B.; Blanchard, J. S. Nat. Struct. Mol. Biol. 2006, 13, 408.
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Nat. Struct. Mol. Biol
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Argyrou, A.1
Vetting, M.W.2
Aladegbami, B.3
Blanchard, J.S.4
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Lutz, J.; Hollmann, F.; Ho, T. V.; Schnyder, A.; Fish, R. H.; Schmid, A. J. Organomet Chem. 2004, 689, 4783.
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J. Organomet Chem
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Lutz, J.1
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Schnyder, A.4
Fish, R.H.5
Schmid, A.6
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24
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Behnke, D.; Taube, R.; Illgen, K.; Nerdinger, S.; Herdtweck, E. Synlett 2004, 688.
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Synlett
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Behnke, D.1
Taube, R.2
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Nerdinger, S.4
Herdtweck, E.5
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25
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0033551720
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For different trappings, see
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For different trappings, see: Livinghouse, T. Tetrahedron 1999, 55, 9947.
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(1999)
Tetrahedron
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Livinghouse, T.1
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26
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84982077736
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For a Ugi-type process upon a quinolininium salt, see
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(a) For a Ugi-type process upon a quinolininium salt, see: Ugi, I.; Böttner, E. Liebigs Ann. Chem. 1963, 670, 74.
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(1963)
Liebigs Ann. Chem
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Ugi, I.1
Böttner, E.2
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27
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33846314518
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Also see ref 2a
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(b) Also see ref 2a.
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28
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1242316919
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Ma, Z.; Hano, Y.; Nomura, T.; Chen, Y. Bioorg. Med. Chem. Lett. 2004, 14, 1193.
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Bioorg. Med. Chem. Lett
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Ma, Z.1
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Nomura, T.3
Chen, Y.4
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30
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33846270871
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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
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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.
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31
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0028939577
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For an approach to this structural class, see
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For an approach to this structural class, see: Lavilla, R.; Gotsens, T.; Guerrero, M.; Bosch, J. Synthesis 1995, 382.
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(1995)
Synthesis
, pp. 382
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Lavilla, R.1
Gotsens, T.2
Guerrero, M.3
Bosch, J.4
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33
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0026051825
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(b) Amann, R.; Spitzner, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1320.
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(1991)
Angew. Chem., Int. Ed. Engl
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Amann, R.1
Spitzner, D.2
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34
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More than 75,800 substances with the nicotinonitrile core are listed in SciFinder (2006), most of them in biomedical patents.
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(a) More than 75,800 substances with the nicotinonitrile core are listed in SciFinder (2006), most of them in biomedical patents.
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35
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Interestingly the cyano substituent is the synthetic precursor for the tetrazole moiety. For a recent result, see
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(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.
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(2006)
Tetrahedron
, vol.62
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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
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