A new color of the synthetic chameleon methoxyallene: Synthesis of trifluoromethyl-substituted pyridinol derivatives: An unusual reaction mechanism, a remarkable crystal packing, and first palladium-catalyzed coupling reactions

Chemistry - A European Journal

Volumn 10, Issue 17, 2004, Pages 4283-4290

  Flögel, Oliver ^a   Dash, Jyotirmayee ^a   Brüdgam, Irene ^a   Hartl, Hans ^a   Reißig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Allenes; Cyclization; Palladium; Pyridines; Supramolecular chemistry

Indexed keywords

ADDITION REACTIONS; CATALYSIS; DERIVATIVES; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CRYSTAL PACKING; CYCLIZATION; SUPRAMOLECULAR ARRANGEMENT; TRIPOLAR SYNTHONS;

AROMATIC POLYMERS;

ALLENE DERIVATIVE; FLUORINE DERIVATIVE; NITRILE; PALLADIUM; PYRIDINE DERIVATIVE; PYRIDINOL; PYRROLE DERIVATIVE; SILVER NITRATE; TRIFLUOROACETIC ACID;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CATALYSIS; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; CYCLIZATION; QUANTUM YIELD; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 4644262365     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400322     Document Type: Article

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34. b) A unique synthesis of pyridine derivatives starting from nitriles and allenylmagnesium bromide was found by H. Hopf and H. H. W. Lautenbach, but it introduces two molecules of nitrile into the pyridine and follows an entirely different mechanism: H. H. W. Lautenbach, Dissertation, Technische Universität Braunschweig, 1991. We thank Prof. H. Hopf for informing us about this interesting unpublished result.
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37. Recent results demonstrate that several other nitriles can be employed in this new pyridine synthesis. J. Dash unpublished results. 2004.
38. A high percentage of newly registered drugs (10%) and crop-protection agents (40%) contain one or more fluorine atoms. Organic-Chemical Drugs and their Synonyms (Ed.: M. Negwer), Akademie, Berlin, 1994; Annual Reports in Medicinal Chemistry, Vols. 34-36 (Ed.: A. M. Doherty). Academic Press, San Diego 1999-2001; J. G. Dingwall, Pestic. Sci. 1994, 41, 259-267. See also: M. J. Silvester, Aldrichimica Acta 1991, 24, 31. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (Eds.: R. Filler, Y. Kobayashi, L. M. Yagupolskii), Elsevier, Amsterdam, 1993; M. A. McClinton. D. A. McClinton, Tetrahedron 1992, 48, 6555-6666; P. Lin, J. Jiang, Tetrahedron 2000, 56, 3635-3671.
39. A high percentage of newly registered drugs (10%) and crop-protection agents (40%) contain one or more fluorine atoms. Organic-Chemical Drugs and their Synonyms (Ed.: M. Negwer), Akademie, Berlin, 1994; Annual Reports in Medicinal Chemistry, Vols. 34-36 (Ed.: A. M. Doherty). Academic Press, San Diego 1999-2001; J. G. Dingwall, Pestic. Sci. 1994, 41, 259-267. See also: M. J. Silvester, Aldrichimica Acta 1991, 24, 31. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (Eds.: R. Filler, Y. Kobayashi, L. M. Yagupolskii), Elsevier, Amsterdam, 1993; M. A. McClinton. D. A. McClinton, Tetrahedron 1992, 48, 6555-6666; P. Lin, J. Jiang, Tetrahedron 2000, 56, 3635-3671.
40. A high percentage of newly registered drugs (10%) and crop-protection agents (40%) contain one or more fluorine atoms. Organic-Chemical Drugs and their Synonyms (Ed.: M. Negwer), Akademie, Berlin, 1994; Annual Reports in Medicinal Chemistry, Vols. 34-36 (Ed.: A. M. Doherty). Academic Press, San Diego 1999-2001; J. G. Dingwall, Pestic. Sci. 1994, 41, 259-267. See also: M. J. Silvester, Aldrichimica Acta 1991, 24, 31. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (Eds.: R. Filler, Y. Kobayashi, L. M. Yagupolskii), Elsevier, Amsterdam, 1993; M. A. McClinton. D. A. McClinton, Tetrahedron 1992, 48, 6555-6666; P. Lin, J. Jiang, Tetrahedron 2000, 56, 3635-3671.
41. A high percentage of newly registered drugs (10%) and crop-protection agents (40%) contain one or more fluorine atoms. Organic-Chemical Drugs and their Synonyms (Ed.: M. Negwer), Akademie, Berlin, 1994; Annual Reports in Medicinal Chemistry, Vols. 34-36 (Ed.: A. M. Doherty). Academic Press, San Diego 1999-2001; J. G. Dingwall, Pestic. Sci. 1994, 41, 259-267. See also: M. J. Silvester, Aldrichimica Acta 1991, 24, 31. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (Eds.: R. Filler, Y. Kobayashi, L. M. Yagupolskii), Elsevier, Amsterdam, 1993; M. A. McClinton. D. A. McClinton, Tetrahedron 1992, 48, 6555-6666; P. Lin, J. Jiang, Tetrahedron 2000, 56, 3635-3671.
42. A high percentage of newly registered drugs (10%) and crop-protection agents (40%) contain one or more fluorine atoms. Organic-Chemical Drugs and their Synonyms (Ed.: M. Negwer), Akademie, Berlin, 1994; Annual Reports in Medicinal Chemistry, Vols. 34-36 (Ed.: A. M. Doherty). Academic Press, San Diego 1999-2001; J. G. Dingwall, Pestic. Sci. 1994, 41, 259-267. See also: M. J. Silvester, Aldrichimica Acta 1991, 24, 31. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (Eds.: R. Filler, Y. Kobayashi, L. M. Yagupolskii), Elsevier, Amsterdam, 1993; M. A. McClinton. D. A. McClinton, Tetrahedron 1992, 48, 6555-6666; P. Lin, J. Jiang, Tetrahedron 2000, 56, 3635-3671.
43. A high percentage of newly registered drugs (10%) and crop-protection agents (40%) contain one or more fluorine atoms. Organic-Chemical Drugs and their Synonyms (Ed.: M. Negwer), Akademie, Berlin, 1994; Annual Reports in Medicinal Chemistry, Vols. 34-36 (Ed.: A. M. Doherty). Academic Press, San Diego 1999-2001; J. G. Dingwall, Pestic. Sci. 1994, 41, 259-267. See also: M. J. Silvester, Aldrichimica Acta 1991, 24, 31. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (Eds.: R. Filler, Y. Kobayashi, L. M. Yagupolskii), Elsevier, Amsterdam, 1993; M. A. McClinton. D. A. McClinton, Tetrahedron 1992, 48, 6555-6666; P. Lin, J. Jiang, Tetrahedron 2000, 56, 3635-3671.
44. A high percentage of newly registered drugs (10%) and crop-protection agents (40%) contain one or more fluorine atoms. Organic-Chemical Drugs and their Synonyms (Ed.: M. Negwer), Akademie, Berlin, 1994; Annual Reports in Medicinal Chemistry, Vols. 34-36 (Ed.: A. M. Doherty). Academic Press, San Diego 1999-2001; J. G. Dingwall, Pestic. Sci. 1994, 41, 259-267. See also: M. J. Silvester, Aldrichimica Acta 1991, 24, 31. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (Eds.: R. Filler, Y. Kobayashi, L. M. Yagupolskii), Elsevier, Amsterdam, 1993; M. A. McClinton. D. A. McClinton, Tetrahedron 1992, 48, 6555-6666; P. Lin, J. Jiang, Tetrahedron 2000, 56, 3635-3671.
45. For selected syntheses of trifluoromethyl-substituted pyridine derivatives, see: L. F. Lee, J. E. Normansell, J. Org. Chem. 1990, 55, 2964-2967; S. G. Hedge, J. Org. Chem. 1991, 56, 5726-5729; F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2002, 327-330; V. Y. Sosnovskikh, B. I. Usachev, A. Y. Sizov, I. I. Vorontsov, Y. V. Shkiyaev, Org. Lett. 2003, 5, 3123-3126.
46. For selected syntheses of trifluoromethyl-substituted pyridine derivatives, see: L. F. Lee, J. E. Normansell, J. Org. Chem. 1990, 55, 2964-2967; S. G. Hedge, J. Org. Chem. 1991, 56, 5726-5729; F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2002, 327-330; V. Y. Sosnovskikh, B. I. Usachev, A. Y. Sizov, I. I. Vorontsov, Y. V. Shkiyaev, Org. Lett. 2003, 5, 3123-3126.
47. For selected syntheses of trifluoromethyl-substituted pyridine derivatives, see: L. F. Lee, J. E. Normansell, J. Org. Chem. 1990, 55, 2964-2967; S. G. Hedge, J. Org. Chem. 1991, 56, 5726-5729; F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2002, 327-330; V. Y. Sosnovskikh, B. I. Usachev, A. Y. Sizov, I. I. Vorontsov, Y. V. Shkiyaev, Org. Lett. 2003, 5, 3123-3126.
48. For selected syntheses of trifluoromethyl-substituted pyridine derivatives, see: L. F. Lee, J. E. Normansell, J. Org. Chem. 1990, 55, 2964-2967; S. G. Hedge, J. Org. Chem. 1991, 56, 5726-5729; F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2002, 327-330; V. Y. Sosnovskikh, B. I. Usachev, A. Y. Sizov, I. I. Vorontsov, Y. V. Shkiyaev, Org. Lett. 2003, 5, 3123-3126.
49. The pyridine tautomer of our pyridinols may also act as a ligand for iron ions: S. Piyamongkol, Z. D. Liu, R. C. Hider, Tetrahedron 2001, 57, 3479-3486.
50. Alkenyl and aryl nonaflates as partners in palladium-catalyzed reactions: S. Bräse, A. de Meijere, Angew. Chem. 1995, 107, 2741-2743; Angew. Chem. Int. Ed. Engl. 1995, 34, 2545; M. Webel, H.-U. Reißig, Synlett 1997, 1141-1142; K. Voigt, P. von Zezschwitz, K. Rosauer, A. Lansky, A. Adams, O. Reiser, A. de Meijere, Eur. J. Org. Chem. 1998, 1521-1534; M. Rottlaender, P. Knochel, J. Org. Chem. 1998, 63, 203-208; S. Bräse, Synlett 1999, 1654-1656; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Synlett 2001, 1293-1295; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2001, 4189-4194; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 1015-1025; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 3646-3658.
51. Alkenyl and aryl nonaflates as partners in palladium-catalyzed reactions: S. Bräse, A. de Meijere, Angew. Chem. 1995, 107, 2741-2743; Angew. Chem. Int. Ed. Engl. 1995, 34, 2545; M. Webel, H.-U. Reißig, Synlett 1997, 1141-1142; K. Voigt, P. von Zezschwitz, K. Rosauer, A. Lansky, A. Adams, O. Reiser, A. de Meijere, Eur. J. Org. Chem. 1998, 1521-1534; M. Rottlaender, P. Knochel, J. Org. Chem. 1998, 63, 203-208; S. Bräse, Synlett 1999, 1654-1656; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Synlett 2001, 1293-1295; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2001, 4189-4194; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 1015-1025; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 3646-3658.
52. Alkenyl and aryl nonaflates as partners in palladium-catalyzed reactions: S. Bräse, A. de Meijere, Angew. Chem. 1995, 107, 2741-2743; Angew. Chem. Int. Ed. Engl. 1995, 34, 2545; M. Webel, H.-U. Reißig, Synlett 1997, 1141-1142; K. Voigt, P. von Zezschwitz, K. Rosauer, A. Lansky, A. Adams, O. Reiser, A. de Meijere, Eur. J. Org. Chem. 1998, 1521-1534; M. Rottlaender, P. Knochel, J. Org. Chem. 1998, 63, 203-208; S. Bräse, Synlett 1999, 1654-1656; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Synlett 2001, 1293-1295; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2001, 4189-4194; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 1015-1025; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 3646-3658.
53. Alkenyl and aryl nonaflates as partners in palladium-catalyzed reactions: S. Bräse, A. de Meijere, Angew. Chem. 1995, 107, 2741-2743; Angew. Chem. Int. Ed. Engl. 1995, 34, 2545; M. Webel, H.-U. Reißig, Synlett 1997, 1141-1142; K. Voigt, P. von Zezschwitz, K. Rosauer, A. Lansky, A. Adams, O. Reiser, A. de Meijere, Eur. J. Org. Chem. 1998, 1521-1534; M. Rottlaender, P. Knochel, J. Org. Chem. 1998, 63, 203-208; S. Bräse, Synlett 1999, 1654-1656; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Synlett 2001, 1293-1295; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2001, 4189-4194; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 1015-1025; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 3646-3658.
54. Alkenyl and aryl nonaflates as partners in palladium-catalyzed reactions: S. Bräse, A. de Meijere, Angew. Chem. 1995, 107, 2741-2743; Angew. Chem. Int. Ed. Engl. 1995, 34, 2545; M. Webel, H.-U. Reißig, Synlett 1997, 1141-1142; K. Voigt, P. von Zezschwitz, K. Rosauer, A. Lansky, A. Adams, O. Reiser, A. de Meijere, Eur. J. Org. Chem. 1998, 1521-1534; M. Rottlaender, P. Knochel, J. Org. Chem. 1998, 63, 203-208; S. Bräse, Synlett 1999, 1654-1656; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Synlett 2001, 1293-1295; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2001, 4189-4194; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 1015-1025; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 3646-3658.
55. Alkenyl and aryl nonaflates as partners in palladium-catalyzed reactions: S. Bräse, A. de Meijere, Angew. Chem. 1995, 107, 2741-2743; Angew. Chem. Int. Ed. Engl. 1995, 34, 2545; M. Webel, H.-U. Reißig, Synlett 1997, 1141-1142; K. Voigt, P. von Zezschwitz, K. Rosauer, A. Lansky, A. Adams, O. Reiser, A. de Meijere, Eur. J. Org. Chem. 1998, 1521-1534; M. Rottlaender, P. Knochel, J. Org. Chem. 1998, 63, 203-208; S. Bräse, Synlett 1999, 1654-1656; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Synlett 2001, 1293-1295; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2001, 4189-4194; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 1015-1025; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 3646-3658.
56. Alkenyl and aryl nonaflates as partners in palladium-catalyzed reactions: S. Bräse, A. de Meijere, Angew. Chem. 1995, 107, 2741-2743; Angew. Chem. Int. Ed. Engl. 1995, 34, 2545; M. Webel, H.-U. Reißig, Synlett 1997, 1141-1142; K. Voigt, P. von Zezschwitz, K. Rosauer, A. Lansky, A. Adams, O. Reiser, A. de Meijere, Eur. J. Org. Chem. 1998, 1521-1534; M. Rottlaender, P. Knochel, J. Org. Chem. 1998, 63, 203-208; S. Bräse, Synlett 1999, 1654-1656; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Synlett 2001, 1293-1295; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2001, 4189-4194; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 1015-1025; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 3646-3658.
57. Alkenyl and aryl nonaflates as partners in palladium-catalyzed reactions: S. Bräse, A. de Meijere, Angew. Chem. 1995, 107, 2741-2743; Angew. Chem. Int. Ed. Engl. 1995, 34, 2545; M. Webel, H.-U. Reißig, Synlett 1997, 1141-1142; K. Voigt, P. von Zezschwitz, K. Rosauer, A. Lansky, A. Adams, O. Reiser, A. de Meijere, Eur. J. Org. Chem. 1998, 1521-1534; M. Rottlaender, P. Knochel, J. Org. Chem. 1998, 63, 203-208; S. Bräse, Synlett 1999, 1654-1656; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Synlett 2001, 1293-1295; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2001, 4189-4194; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 1015-1025; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 3646-3658.
58. Alkenyl and aryl nonaflates as partners in palladium-catalyzed reactions: S. Bräse, A. de Meijere, Angew. Chem. 1995, 107, 2741-2743; Angew. Chem. Int. Ed. Engl. 1995, 34, 2545; M. Webel, H.-U. Reißig, Synlett 1997, 1141-1142; K. Voigt, P. von Zezschwitz, K. Rosauer, A. Lansky, A. Adams, O. Reiser, A. de Meijere, Eur. J. Org. Chem. 1998, 1521-1534; M. Rottlaender, P. Knochel, J. Org. Chem. 1998, 63, 203-208; S. Bräse, Synlett 1999, 1654-1656; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Synlett 2001, 1293-1295; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2001, 4189-4194; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 1015-1025; I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 3646-3658.
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