Preparation of non-symmetrical 2,3-bis-(2,2'-oligopyridyl)pyrazines via 1,2-disubstituted ethanones

Synlett

Volumn , Issue 8, 1999, Pages 1203-1206

  Heirtzler, Fenton R ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

C C coupling; Enol; Oxidation; Pyrazine; Pyridine

Indexed keywords

PYRAZINE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; POLYMERIZATION;

EID: 0032783151     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2800     Document Type: Article

References (37)

1. Chan, C.-W.; Mingos, D. M. P.; White, A. J. P.; Williams, D. J. Chem. Commun. 1996, 81; Ferigo, M.; Bonhôte, P.; Marty, W.; Stoeckli-Evans, H. J. Chem. Soc., Dalton Trans. 1994, 1549; Neels, A.; Stoeckli-Evans, H.; Escuer, A.; Vicente, R. Inorg. Chem. 1995, 34, 1846; Campagna, S.; Denti, G.; Serroni, S.; Juris, A.; Venturi, M.; Ricevuto, V.; Balzani, V. Chem. Eur. J. 1995, 1, 21; Brauns, E.; Jones, S. W.; Clark, J. A.; Molnar, S. M.; Kawanishi, Y.; Brewer, K. J. Inorg. Chem. 1997, 56, 2861.
2. Chan, C.-W.; Mingos, D. M. P.; White, A. J. P.; Williams, D. J. Chem. Commun. 1996, 81; Ferigo, M.; Bonhôte, P.; Marty, W.; Stoeckli-Evans, H. J. Chem. Soc., Dalton Trans. 1994, 1549; Neels, A.; Stoeckli-Evans, H.; Escuer, A.; Vicente, R. Inorg. Chem. 1995, 34, 1846; Campagna, S.; Denti, G.; Serroni, S.; Juris, A.; Venturi, M.; Ricevuto, V.; Balzani, V. Chem. Eur. J. 1995, 1, 21; Brauns, E.; Jones, S. W.; Clark, J. A.; Molnar, S. M.; Kawanishi, Y.; Brewer, K. J. Inorg. Chem. 1997, 56, 2861.
3. Chan, C.-W.; Mingos, D. M. P.; White, A. J. P.; Williams, D. J. Chem. Commun. 1996, 81; Ferigo, M.; Bonhôte, P.; Marty, W.; Stoeckli-Evans, H. J. Chem. Soc., Dalton Trans. 1994, 1549; Neels, A.; Stoeckli-Evans, H.; Escuer, A.; Vicente, R. Inorg. Chem. 1995, 34, 1846; Campagna, S.; Denti, G.; Serroni, S.; Juris, A.; Venturi, M.; Ricevuto, V.; Balzani, V. Chem. Eur. J. 1995, 1, 21; Brauns, E.; Jones, S. W.; Clark, J. A.; Molnar, S. M.; Kawanishi, Y.; Brewer, K. J. Inorg. Chem. 1997, 56, 2861.
4. Chan, C.-W.; Mingos, D. M. P.; White, A. J. P.; Williams, D. J. Chem. Commun. 1996, 81; Ferigo, M.; Bonhôte, P.; Marty, W.; Stoeckli-Evans, H. J. Chem. Soc., Dalton Trans. 1994, 1549; Neels, A.; Stoeckli-Evans, H.; Escuer, A.; Vicente, R. Inorg. Chem. 1995, 34, 1846; Campagna, S.; Denti, G.; Serroni, S.; Juris, A.; Venturi, M.; Ricevuto, V.; Balzani, V. Chem. Eur. J. 1995, 1, 21; Brauns, E.; Jones, S. W.; Clark, J. A.; Molnar, S. M.; Kawanishi, Y.; Brewer, K. J. Inorg. Chem. 1997, 56, 2861.
5. Chan, C.-W.; Mingos, D. M. P.; White, A. J. P.; Williams, D. J. Chem. Commun. 1996, 81; Ferigo, M.; Bonhôte, P.; Marty, W.; Stoeckli-Evans, H. J. Chem. Soc., Dalton Trans. 1994, 1549; Neels, A.; Stoeckli-Evans, H.; Escuer, A.; Vicente, R. Inorg. Chem. 1995, 34, 1846; Campagna, S.; Denti, G.; Serroni, S.; Juris, A.; Venturi, M.; Ricevuto, V.; Balzani, V. Chem. Eur. J. 1995, 1, 21; Brauns, E.; Jones, S. W.; Clark, J. A.; Molnar, S. M.; Kawanishi, Y.; Brewer, K. J. Inorg. Chem. 1997, 56, 2861.
6. Schnebeck, R.-D.; Randaccio, L.; Zangrando, E.; Lippert, B. Angew. Chem. Int. Ed. 1998, 37, 119.
7. Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Am. Chem. Soc. 1995, 117, 4562.
8. Bark, T.; Weyhermüller, T.; Heirtzler, F. Chem. Commun. 1998, 1475.
9. Heirtzler, F. R.; Neuburger, M.; Zehnder, M.; Constable, E. C. Liebigs Ann./Recueil 1997, 297.
10. Heirtzler, F.; Weyhermüller, T. J. Chem. Soc., Dalton Trans. 1997, 3653; Heirtzler, F. R.; Neuburger, M.; Zehnder, M.; Bird, S. J.; Orrell, K. G.; Sik, V. J. Chem. Soc., Dalton Trans. 1999, 565; Heirtzler, F.; Jones, P. G.; Neuburger, M.; Zehnder, M. Polyhedron 1999, 18, 601.
11. Heirtzler, F.; Weyhermüller, T. J. Chem. Soc., Dalton Trans. 1997, 3653; Heirtzler, F. R.; Neuburger, M.; Zehnder, M.; Bird, S. J.; Orrell, K. G.; Sik, V. J. Chem. Soc., Dalton Trans. 1999, 565; Heirtzler, F.; Jones, P. G.; Neuburger, M.; Zehnder, M. Polyhedron 1999, 18, 601.
12. Heirtzler, F.; Weyhermüller, T. J. Chem. Soc., Dalton Trans. 1997, 3653; Heirtzler, F. R.; Neuburger, M.; Zehnder, M.; Bird, S. J.; Orrell, K. G.; Sik, V. J. Chem. Soc., Dalton Trans. 1999, 565; Heirtzler, F.; Jones, P. G.; Neuburger, M.; Zehnder, M. Polyhedron 1999, 18, 601.
13. Thummel, R. P.; Jahng, Y. J. Org. Chem. 1985, 50, 3635; Wenkert, D.; Woodward, R. B. J. Org. Chem. 1983, 48, 283.
14. Thummel, R. P.; Jahng, Y. J. Org. Chem. 1985, 50, 3635; Wenkert, D.; Woodward, R. B. J. Org. Chem. 1983, 48, 283.
15. Fife, W. K. J. Org. Chem. 1983, 48, 1375.
16. 4: C, 74.41; H, 3.90; N, 21.69. Found: C, 73.82; H, 4.10; N, 21.00.
17. 5c: Baxter, P. N. W.; Connor, J. A.; Joseph, A.; Schweizer, W. B.; Wallis, J. D. J. Chem. Soc., Dalton Trans. 1992, 3015.
18. 2: C, 67.28; H, 4.71; N, 13.08. Found: C, 67.23; H, 4.88; N, 12.88.
19. (a) Buhleier, E.; Wehner, W.; Vögtle, F. Chem. Ber. 1978, 111, 201; Potts, K. T. Bull. Soc. Chim. Belg. 1990, 99, 741; König, B. Chem. Ber. 1995, 128, 1141;
20. (a) Buhleier, E.; Wehner, W.; Vögtle, F. Chem. Ber. 1978, 111, 201; Potts, K. T. Bull. Soc. Chim. Belg. 1990, 99, 741; König, B. Chem. Ber. 1995, 128, 1141;
21. (a) Buhleier, E.; Wehner, W.; Vögtle, F. Chem. Ber. 1978, 111, 201; Potts, K. T. Bull. Soc. Chim. Belg. 1990, 99, 741; König, B. Chem. Ber. 1995, 128, 1141;
22. (b) Case, F. H. J. Org. Chem. 1966, 31, 2398.
23. 3O: C, 74.17; H, 4.76; N, 15.26. Found: C, 74.42; H, 5.26; N, 14.52.
24. Newkome, G. R.; Roper, J. M.; Robinson, M. J. J. Org. Chem. 1980, 45, 4380; Rabjohn, N. Org. React. (N.Y.); Dauben, W. G., Ed.; 1976, 24, 261.
25. Newkome, G. R.; Roper, J. M.; Robinson, M. J. J. Org. Chem. 1980, 45, 4380; Rabjohn, N. Org. React. (N.Y.); Dauben, W. G., Ed.; 1976, 24, 261.
26. 2: C, 70.58; H, 3.83; N, 14.53. Found: C, 70.30; H, 3.86; N, 14.43.
27. Rubottom, G. M.; Juve, H. D. J. Org. Chem. 1983, 48, 422.
28. Krow, G. R. Org. React. (N.Y.); Paquette, L. A., Ed.; 1993, 43, 251.
29. E.g., bromine, iodine, magnesium monoperoxyphthalic acid, peracetic acid, Davis's oxiranc, Brederick's reagent and pyridinium chlorochromate. See: Bonadies, F.; Bonini, C. Synth. Commun. 1988, 18, 1573; Davis, F. A.; Sheppard, A. C. J. Org. Chem. 1987, 52, 954; Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573; Eistert, B.; Endres, E. Liebigs Ann. 1970, 734, 56; Vogel, E.; Klug, W.; Breuer, A. Organic Syntheses, Coll. Vol. 6; Noland, W. E. Ed.; Wiley: New York, 1988.
30. E.g., bromine, iodine, magnesium monoperoxyphthalic acid, peracetic acid, Davis's oxiranc, Brederick's reagent and pyridinium chlorochromate. See: Bonadies, F.; Bonini, C. Synth. Commun. 1988, 18, 1573; Davis, F. A.; Sheppard, A. C. J. Org. Chem. 1987, 52, 954; Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573; Eistert, B.; Endres, E. Liebigs Ann. 1970, 734, 56; Vogel, E.; Klug, W.; Breuer, A. Organic Syntheses, Coll. Vol. 6; Noland, W. E. Ed.; Wiley: New York, 1988.
31. E.g., bromine, iodine, magnesium monoperoxyphthalic acid, peracetic acid, Davis's oxiranc, Brederick's reagent and pyridinium chlorochromate. See: Bonadies, F.; Bonini, C. Synth. Commun. 1988, 18, 1573; Davis, F. A.; Sheppard, A. C. J. Org. Chem. 1987, 52, 954; Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573; Eistert, B.; Endres, E. Liebigs Ann. 1970, 734, 56; Vogel, E.; Klug, W.; Breuer, A. Organic Syntheses, Coll. Vol. 6; Noland, W. E. Ed.; Wiley: New York, 1988.
32. E.g., bromine, iodine, magnesium monoperoxyphthalic acid, peracetic acid, Davis's oxiranc, Brederick's reagent and pyridinium chlorochromate. See: Bonadies, F.; Bonini, C. Synth. Commun. 1988, 18, 1573; Davis, F. A.; Sheppard, A. C. J. Org. Chem. 1987, 52, 954; Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573; Eistert, B.; Endres, E. Liebigs Ann. 1970, 734, 56; Vogel, E.; Klug, W.; Breuer, A. Organic Syntheses, Coll. Vol. 6; Noland, W. E. Ed.; Wiley: New York, 1988.
33. E.g., bromine, iodine, magnesium monoperoxyphthalic acid, peracetic acid, Davis's oxiranc, Brederick's reagent and pyridinium chlorochromate. See: Bonadies, F.; Bonini, C. Synth. Commun. 1988, 18, 1573; Davis, F. A.; Sheppard, A. C. J. Org. Chem. 1987, 52, 954; Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573; Eistert, B.; Endres, E. Liebigs Ann. 1970, 734, 56; Vogel, E.; Klug, W.; Breuer, A. Organic Syntheses, Coll. Vol. 6; Noland, W. E. Ed.; Wiley: New York, 1988.
34. 5: C, 73.30; H, 4.21; N, 22.49. Found: C, 73.17; H, 4.36; N, 22.84.
35. Constable, E. C. Tetrahedron 1992, 48, 10013; Bassani, D. M.; Lehn, J.-M.; Baum, G.; Fenske, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1845.
36. Constable, E. C. Tetrahedron 1992, 48, 10013; Bassani, D. M.; Lehn, J.-M.; Baum, G.; Fenske, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1845.
37. See: Boyd, D. R.; Evans, T. A.; Jennings, W. B.; Malone, J. F.; O'Sullivan, W.; Smith, A. J. Chem. Soc., Chem. Commun. 1996, 2269.