A facile and convenient synthesis of 1,2,3,6-tetrahydropyridazines using azodicarboxylates under lanthanum triflate catalysis

Heterocycles

Volumn 55, Issue 8, 2001, Pages 1599-1604

  Curini, Massimo ^a   Epifano, Francesco ^a   Marcotullio, Maria Carla ^a   Rosati, Ornelio ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001142630     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-01-9272     Document Type: Article

References (21)

1. a) S. M. Weinreb and R. R. Staib, Tetrahedron, 1982, 38, 3087;
2. b) T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 245.
3. O. Diels, J. H. Blom, and W. Koll, Ann. Chem., 1925, 443, 242.
4. For selected examples of hetero-Diels-Alder reactions using azodicarboxylates see: a) A. Shah and M. V. George, Tetrahedron, 1971, 27, 1291; b) G. Kresze, M. Morper, and A. Bijev, Tetrahedron Lett., 1977, 2259; H. Hiranuma and S. I. Miller, J. Org. Chem., 1983, 48, 3096; A. Toepfer and R. R. Schmidt, Carbohydr. Res., 1993, 247, 159; e) S. Moriyama, T. Mochizuki, Y. Ohshima, and T. Saito, Bull. Chem. Soc. Jpn., 1994, 67, 2876.
5. For selected examples of hetero-Diels-Alder reactions using azodicarboxylates see: a) A. Shah and M. V. George, Tetrahedron, 1971, 27, 1291; b) G. Kresze, M. Morper, and A. Bijev, Tetrahedron Lett., 1977, 2259; H. Hiranuma and S. I. Miller, J. Org. Chem., 1983, 48, 3096; A. Toepfer and R. R. Schmidt, Carbohydr. Res., 1993, 247, 159; e) S. Moriyama, T. Mochizuki, Y. Ohshima, and T. Saito, Bull. Chem. Soc. Jpn., 1994, 67, 2876.
6. For selected examples of hetero-Diels-Alder reactions using azodicarboxylates see: a) A. Shah and M. V. George, Tetrahedron, 1971, 27, 1291; b) G. Kresze, M. Morper, and A. Bijev, Tetrahedron Lett., 1977, 2259; H. Hiranuma and S. I. Miller, J. Org. Chem., 1983, 48, 3096; A. Toepfer and R. R. Schmidt, Carbohydr. Res., 1993, 247, 159; e) S. Moriyama, T. Mochizuki, Y. Ohshima, and T. Saito, Bull. Chem. Soc. Jpn., 1994, 67, 2876.
7. For selected examples of hetero-Diels-Alder reactions using azodicarboxylates see: a) A. Shah and M. V. George, Tetrahedron, 1971, 27, 1291; b) G. Kresze, M. Morper, and A. Bijev, Tetrahedron Lett., 1977, 2259; H. Hiranuma and S. I. Miller, J. Org. Chem., 1983, 48, 3096; A. Toepfer and R. R. Schmidt, Carbohydr. Res., 1993, 247, 159; e) S. Moriyama, T. Mochizuki, Y. Ohshima, and T. Saito, Bull. Chem. Soc. Jpn., 1994, 67, 2876.
8. For selected examples of hetero-Diels-Alder reactions using azodicarboxylates see: a) A. Shah and M. V. George, Tetrahedron, 1971, 27, 1291; b) G. Kresze, M. Morper, and A. Bijev, Tetrahedron Lett., 1977, 2259; H. Hiranuma and S. I. Miller, J. Org. Chem., 1983, 48, 3096; A. Toepfer and R. R. Schmidt, Carbohydr. Res., 1993, 247, 159; e) S. Moriyama, T. Mochizuki, Y. Ohshima, and T. Saito, Bull. Chem. Soc. Jpn., 1994, 67, 2876.
9. M. Avalos, R. Babiano, P. Cintas, F. R. Clemente, J. L. Jimenez, J. C. Palacios, and J. B. Sanchez, J. Org. Chem., 1999, 64, 6297 and references cited herein.
10. C. Qian and L. Wang, Tetrahedron, 2000, 56, 7193.
11. S. Kobayashi, I. Hachiya, M. Araki, and H. Ishitani, Tetrahedron Lett., 1993, 34, 3755.
12. L. B. Yu, D. P. Chen, and P. G. Wang, Tetrahedron Lett., 1996, 37, 2169.
13. C. Qian and L. Wang, Tetrahedron Lett., 2000, 41, 2203.
14. M. Curini, F. Epifano, M. C. Marcotullio, and O. Rosati, Tetrahedron Lett., 2001, 42, 3159.
15. a) I. H. Aspinall, P. M. Cowley, G. Mitchell, C. M. Raynor, and R. J. Stoodley, J. Chem. Soc., Perkin Trans. 1, 1999, 2591 and references cited herein;
16. b) L. Zhang, M. A. Williams, D. B. Mendel, P. A. Escarpe, X. Chen., K. Y. Wang, B. J. Graves, G. Lawton, and C. U. Kim, Bioorg. Med. Chem. Lett., 1999, 9, 1751.
17. A. K Forrest and R. R. Schmidt, Tetrahedron Lett., 1984, 25, 1769.
18. G. Jenner and R. Ben Salem, J. Chem. Soc., Perkin Trans. 2, 1990, 1961 and references cited herein.
19. G. De Simoni, G. Faita, P. P. Righetti, and L. Toma, Tetrahedron, 1990, 46, 7951.
20. T. H. Fisher, J. C. Crook, and S. Chang, Tetrahedron, 1987, 43, 2443.
21. Y. Nomura, N. Masai, and Y. Takeuchi, J. Chem. Soc., Chem. Comm., 1975, 307.