Synthesis of unsymmetrical annulated 2,2′-bipyridine analogues with attached cycloalkene and piperidine rings via sequential diels-alder reaction of 5,5′-bi-1,2,4-triazines

Molecules

Volumn 10, Issue 1, 2005, Pages 265-273

  Branowska, D ^a  

^a SIEDLCE UNIVERSITY OF NATURAL SCIENCES AND HUMANITIES   (Poland)

Author keywords

bi 1,2,4 triazines; Diels alder reaction; Isocyclic and heterocyclic enamines

Indexed keywords

1 METHYL 4 PYRROLIDIN 1 YL 1,2,3,6 TETRAHYDROPYRIDINE; 1,2,4 TRIAZINE DERIVATIVE; 2,2' BIPYRIDINE DERIVATIVE; 3,3' BIS(METHYLSULFANYL) 5,5' BIS 1,2,4 TRIAZINE; CYCLOALKANE DERIVATIVE; ENAMINE; NAPHTHYRIDINE DERIVATIVE; PIPERIDINE DERIVATIVE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CYCLOADDITION; DIELS ALDER REACTION; REACTION ANALYSIS;

EID: 15544380224     PISSN: 14203049     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/10010265     Document Type: Article

References (29)

1. Lipinska, T. Tetrahedron Lett. 2004, 45, 8831.
2. Kaes, C.; Katz, A.; Hosseini, M.W. Chem. Rev. 2000, 100, 3553.
3. a) Pietraszkiewicz, M.; Karpiuk, J.; Pietraszkiewicz, O. Spectrochim. Acta Part A 1998, 54, 2229 and references cited therein;
4. b) Pietraszkiewicz, M. Comprehensive Supramolecular Chemistry; Lehn, J.-M.; Kaes, C.; Katz, A.; Hosseini, M. (Eds.) Luminescent Probes; Pergamon: Oxford, U.K. 1996, 10, 225.
5. a) Ito, K.; Yoshitake, M.; Katuski, T. Tetrahedron 1996, 52, 3905;
6. b) Malkov, A.V.; Baxendale, I. R.; Bella, M.; Langer, V.; Fawcett, J.; Russell, D. R.; Mansfield, D. J.; Valko, M.; Kocovsky, P. Organometallics 2001, 20, 673;
7. c) Lötscher, D.; Rupprecht, H.; Stoeckli-Evans, H.; von Zalewsky, A. Tetrahedron-Asymmetr. 2000, 11, 4341;
8. d) Chelucci, G.; Gladiali, S.; Sanna, M. G.; Brunner, H. Tetrahedron-Asymmetr. 2000, 11, 3419.
9. Collomb, P.; von Zalewsky, A. Tetrahedron-Asymmetr. 1998, 9, 3911.
10. Gladiali, S.; Pinna, L.; Delogu, G.; Graf, E.; Brunner, H. Tetrahedron-Asymmetr. 1990, 1, 937.
11. a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron-Asymmetr. 1998, 9, 531;
12. b) Chelucci, G.; Saba, A.; Sanna, G.; Soccolini, F. Tetrahedron-Asymmetr. 2000, 11, 3427.
13. Steel, P. J. Adv. Heterocyclic Chem. 1997, 67, 1.
14. a) Ito, K.; Tabuchi, S.; Katuski, T. Synlett 1992, 575;
15. b) Ito, K.; Katuski, T. Tetrahedron Lett. 1993, 34, 2661.
16. Hayoz, P.; von Zalewsky, A. Tetrahedron Lett. 1992, 33, 5165.
17. Varella, J. A.; Castedo, L.; Maestro, M.; Mahia, J.; Saci, C. Chem. Eur. J. 2001, 7, 5203.
18. Bushby, M.; Moody, C. J.; Riddick D. A.; Waldron, I. R., J. Chem. Soc., Perkin Trans.1 2001, 2183.
19. Rickborn, B. In Organic Reactions; Paquette L. A. (Ed.); J. Wiley and Sons: New York, 1998; 53, 493.
20. Rykowski, A.; Branowska, D.; Kielak, J. Tetrahedron Lett. 2000, 41, 3657.
21. Branowska, D. and Rykowski, A. Synlett, 2002, 1892.
22. Branowska, D. Synthesis, 2003, 2096.
23. Krass, D. K.; Chen, T.-K.; Paudler W. W. J. Heterocyclic Chem, 1973, 10, 343.
24. Rykowski, A.; Lipinska, T. Polish J. Chem. 1997, 71, 83.
25. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1993, 115, 872.
26. Branowska, D. Tetrahedron, 2004, 60, 6021.
27. Perrin D.D.; Armarego W.L. F. Purification of Laboratory Chemicals; Pergamon: Oxford, U.K. 1992.
28. Neunhoeffer, H.; Henning, H.-W.; Frühauf , M.; Mutterer, M. Tetrahedron Lett. 1969, 3147.
29. Kuehne, M. E. J. Am. Chem. Soc. 1959, 81, 5400.