The synthesis of heterocyclic derivatives from pyran-2-ones and hydrazine hydrate. Ammonium cerium(IV) nitrate as an efficient oxidant in pyridazine chemistry

Tetrahedron

Volumn 62, Issue 41, 2006, Pages 9718-9725

  Požgan, Franc ^a   Polanc, Slovenko ^a   Kočevar, Marijan ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Ammonium cerium(IV) nitrate; Dehydrogenation; Esters; Heterocycles; Oxidation; Pyridazine 3 carbohydrazides

Indexed keywords

1,4,5,6,7,8,9,10 OCTAHYDROCYCLOOCTA[C]PYRIDAZINE 3 CARBOHYDRAZIDE; 2 PYRONE DERIVATIVE; 3 HYDRAZINO 6 PHENYL 2,3,4,5 TETRAHYDROPYRIDAZINE 3 CARBOHYDRAZIDE; 4 METHYL 6 (PYRIDIN 2 YL) 1,4 DIHYDROPYRIDAZINE 3 CARBOHYDRAZIDE; 4 METHYL 6 (PYRIDIN 2 YL)PYRIDAZINE 3 CARBOHYDRAZIDE; 4,5,6,7,8,9 HEXAHYDRO 1H CYCLOHEPTA[C]PYRIDAZINE 3 CARBOHYDRAZIDE; 5,6,7,8,9,10 HEXAHYDROCYCLOOCTA[C]PYRIDAZINE 3 CARBOHYDRAZIDE; 6 PHENYL 1,4 DIHYDROPYRIDAZINE 3 CARBOHYDRAZIDE; 6 TERT BUTYL 1,4 DIHYDROPYRIDAZINE 3 CARBOHYDRAZIDE; 6 TERT BUTYL 3 HYDRAZINO 2,3,4,5 TETRAHYDROPYRIDAZINE 3 CARBOHYDRAZIDE; 6 TERT BUTYLPYRIDAZINE 3 CARBOHYDRAZIDE; 6,7,8,9 TETRAHYDRO 5H CYCLOHEPTA[C]PYRIDAZINE 3 CARBOHYDRAZIDE; 9 OXO 4,5,6,7,8,9 HEXAHYDRO 1H PYRIDAZINO[3,4 C]AZEPINE 3 CARBOHYDRAZIDE; 9A HYDROXY 9 OXO 4,4A,5,6,7,8,9A OCTAHYDRO 1H PYRIDAZINO[3,4,C]AZEPINE 3 CARBOHYDRAZIDE; AMMONIA; CERIUM; ETHYL 9 OXO 6,7,8,9 TETRAHYDRO 5H PYRIDAZINO[3,4 C]AZEPINE 3 CARBOXYLATE; HETEROCYCLIC COMPOUND; HYDRAZINE DERIVATIVE; METHYL 4 METHYL 6 (PYRIDIN 2 YL)PYRIDAZINE 3 CARBOXYLATE; METHYL 5,6,7,8,9,10 HEXAHYDROCYCLOOCTA[C]PYRIDAZINE 3 CARBOXYLATE; METHYL 6 PHENYLPYRIDAZINE 3 CARBOXYLATE; METHYL 6 TERT BUTYLPYRIDAZINE 3 CARBOXYLATE; METHYL 6,7,8,9 TETRAHYDRO 5H CYCLOHEPTA[C]PYRIDAZINE 3 CARBOXYLATE; METHYL 9 OXO 6,7,8,9 TETRAHYDRO 5H PYRIDAZINO[3,4 C]AZEPINE 3 CARBOXYLATE; NITRATE; OXIDIZING AGENT; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; OXIDATION KINETICS; PRIORITY JOURNAL;

EID: 33748085001     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.061     Document Type: Article

References (54)

1. Coates W.J. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II: Pyridazines and their Benzo Derivatives Vol. 6 (1996), Pergamon, Oxford 1-91
2. Kolar P., and Tišler M. Adv. Heterocycl. Chem. 75 (1999) 167-241
3. Mátyus P., Maes B.U.W., Riedl Z., Hajós G., Lemière G.L.F., Tapolcsányi P., Monsieurs K., Éliás O., Dommisse R.A., and Krajsovszky G. Synlett (2004) 1123-1139
4. Haider N., and Holzer W. In: Yamamoto Y. (Ed). Science of Synthesis Vol. 16 (2004), Thieme, Stuttgart 125-249
5. Haider N., and Holzer W. In: Yamamoto Y. (Ed). Science of Synthesis Vol. 16 (2004), Thieme, Stuttgart 251-313
6. Groziak M.P. In: Gribble G.W., and Joule J.A. (Eds). Progress in Heterocyclic Chemistry Vol. 16 (2004), Elsevier, Amsterdam 347-384
7. Groziak M.P. In: Gribble G.W., and Joule J.A. (Eds). Progress in Heterocyclic Chemistry Vol. 17 (2005), Elsevier, Amsterdam 304-336
8. Heinisch G., and Kopelent-Frank H. In: Ellis G.P., and Luscombe D.K. (Eds). Progress in Medicinal Chemistry: Pharmacologically Active Pyridazine Derivatives. Part 2 Vol. 29 (1992), Elsevier Science B.V., Amsterdam 141-183
9. Gelain A. J. Heterocycl. Chem. 42 (2005) 395-400
10. Avram M., Dinulescu I.G., Marica E., and Nenitzescu C.D. Chem. Ber. 95 (1962) 2248-2253
11. Kotschy A., Novák Z., Vincze Z., Smith D.M., and Hajós G. Tetrahedron Lett. 40 (1999) 6313-6316
12. Balci M., Saraçoǧlu N., and Menzek A. J. Org. Chem. 68 (2003) 7009-7015
13. González-Gómez J.C., Santana L., and Uriarte E. Tetrahedron 61 (2005) 4805-4810
14. Attanasi O.A., Filippone P., Fiorucci C., Foresti E., and Mantellini F. J. Org. Chem. 63 (1998) 9880-9887
15. Razin V.V., Yakovlev M.E., Shataev K.V., and Selivanov S.I. Russ. J. Org. Chem. 40 (2004) 1027-1032
16. Seitz G., Kämpchen T., and Overheu W. Arch. Pharm. 311 (1978) 786-795
17. Stetter H., and Jonas F. Chem. Ber. 114 (1981) 564-580
18. Ban T., Nagai K., Miyamoto Y., Harano K., Yasuda M., and Kanematsu K. J. Org. Chem. 47 (1982) 110-116
19. Heinisch G., and Waglechner R. J. Heterocycl. Chem. 21 (1984) 1727-1731
20. Hoferichter R., Seitz G., and Waßmuth H. Chem. Ber. 122 (1989) 711-714
21. Pippich S., and Bartsch H. Heterocycles 43 (1996) 1967-1979
22. Klindert T., and Seitz G. Synth. Commun. 26 (1996) 2587-2596
23. Görlitzer K., and Behrje H. Pharmazie 51 (1996) 528-536
24. Nair V., Mathew J., and Prabhakaran J. Chem. Soc. Rev. 26 (1997) 127-132
25. Nair V., Panicker S.B., Nair L.G., George T.G., and Augustine A. Synlett (2003) 156-165
26. Dhakshinamoorthy A. Synlett (2005) 3014-3015
27. Štefane B., Kočevar M., and Polanc S. Tetrahedron Lett. 40 (1999) 4429-4432
28. Požgan F., Polanc S., and Kočevar M. Synthesis (2003) 2349-2352
29. Ellis G.P. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry: Pyrans and Fused Pyrans: (ii) Reactivity Vol. 3 (1984), Pergamon, Oxford 647-736
30. Ram V.J., and Srivastava P. Curr. Org. Chem. 5 (2001) 571-599
31. Hepworth J.D., and Heron B.M. In: Gribble G.W., and Joule J.A. (Eds). Progress in Heterocyclic Chemistry Vol. 17 (2005), Elsevier, Amsterdam 33-62
32. For selected examples, see:
33. Kočevar M., Polanc S., Tišler M., and Verček B. Heterocycles 30 (1990) 227-230
34. Trebše P., Polanc S., Kočevar M., Šolmajer T., and Golič Grdadolnik S. Tetrahedron 53 (1997) 1383-1390
35. Vraničar L., Polanc S., and Kočevar M. Tetrahedron 55 (1999) 271-278
36. Trebše P., Vraničar L., Mušič I., Polanc S., Stevens W.C., and Kočevar M. Heterocycles 53 (2000) 1111-1120
37. Kafka S., Trebše P., Polanc S., and Kočevar M. Synlett (2000) 254-256
38. Ješelnik M., Varma R.S., Polanc S., and Kočevar M. Chem. Commun. (2001) 1716-1717
39. Ješelnik M., Varma R.S., Polanc S., and Kočevar M. Green Chem. 4 (2002) 35-38
40. Vraničar L., Meden A., Polanc S., and Kočevar M. J. Chem. Soc., Perkin Trans. 1 (2002) 675-681
41. Vraničar L., Požgan F., Polanc S., and Kočevar M. Amino Acids 24 (2003) 273-280
42. Satish S., Mitra A., and George M.V. Tetrahedron 35 (1979) 277-285
43. Baker J., Hedges W., Timberlake J.W., and Trefonas L.M. J. Heterocycl. Chem. 20 (1983) 855-859
44. Baumann L., and Seitz G. Tetrahedron Lett. 32 (1991) 5949-5952
45. Nakamichi N., Kawashita Y., and Hayashi M. Synthesis (2004) 1015-1020
46. Berger U., Dannhardt G., and Obergrusberger R. Arch. Pharm. 315 (1982) 428-437
47. Hughes P., and Clardy J. J. Org. Chem. 54 (1989) 3260-3264
48. Aspinall I.H., Cowley P.M., Mitchell G., Raynor C.M., and Stoodley R.J. J. Chem. Soc., Perkin Trans. 1 (1999) 2591-2599
49. Ceraulo L., Lamartina L., Migliara O., Petruso S., and Sprio V. Heterocycles 20 (1983) 551-556
50. Mashraqui S.H., and Karnik M.A. Tetrahedron Lett. 39 (1998) 4895-4898
51. Varma R.S., and Kumar D. Tetrahedron Lett. 40 (1999) 21-24
52. 19b
53. Kepe V., Kočevar M., and Polanc S. J. Heterocycl. Chem. 33 (1996) 1707-1710
54. Kočevar M. Acta Chim. Slov. 43 (1996) 143-152