Synthesis of 5-selenoxo-1,2,4-triazole-1-carboxylates from isoselenocyanates and azodicarboxylates

Heterocycles

Volumn 67, Issue 2, 2006, Pages 749-762

  Favero, Francesco ^a   Sommen, Geoffroy L ^a   Linden, Anthony ^a   Heimgartner, Heinz ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646874363     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-S(T)77     Document Type: Article

References (73)

1. Koketsu M., and Ishihara H. Curr. Org. Chem. 7 (2003) 175
2. Shamberger R.J. Biochemistry of Selenium (1983), Plenum Press, New York
3. Alissa E.M., Bahijri S.M., and Ferns G.A. Med. Sci. Monit. 9 (2003) RA9
4. Srivastava P.C., and Robins R.K. J. Med. Chem. 26 (1983) 445
5. Wu W., Murakami K., Koketsu M., Yamada Y., and Saiki I. Anticancer Res. 19 (1999) 5375
6. El-Bayoumy K., and Sinha R. Mutation Research 551 (2004) 181
7. Patrick L. Alternative Med. Chem. 9 (2004) 239
8. Block E. Adv. Exp. Med. & Biol. 401 (1996) 155
9. Block E., Bird S., Tyson J.F., Uden P.C., Zhang X., and Denoyer E. Phosphorus, Sulfur, Silicon & Rel. Elem. 136-8 (1998) 1
10. May S.W. Exp. Opin. Invest. Drugs 11 (2002) 1261
11. Parnham M.J., and Graf E. Prog. Drug. Res. 36 (1991) 9
12. Koketsu M., Ishihara H., Wu W., Murakami K., and Saiki I. Eur. J. Pharm. Sci. 9 (1999) 157
13. May S.W., Wang L., Gill-Woznichak M.M., Browner R.F., Ogonowski A.A., Smith J.B., and Pollock S.H. J. Pharm. Exp. Ther. 283 (1997) 470
14. Göbel T., Gsell L., Hüter O.F., Maienfisch P., Naef R., O'Sullivan A.C., Pitterna T., Rapold T., Seifert G., Sern M., Szczepanski H., and Wadsworth D.J. Pestic. Sci. 55 (1999) 355
15. El-Desoky S.I., Bondock S.B., Etman H.A., Fadda A.A., and Metwally M.A. Sulfur Lett. 26 (2003) 127
16. Lamberth C. J. Sulfur Chem. 25 (2004) 39
17. Kedar R.M., Vidhale N.N., and Chincholkar M.M. Orient. J. Chem. 12 (1996) 301
18. Metwally M.A., Abdel-Latif E., Amer F.A., and Kaupp G. J. Sulfur Chem. 25 (2004) 63
19. Erol D.D., Aytemir M.D., and Yulug N. Eur. J. Med. Chem. 31 (1996) 731
20. Zhou Y., and Heimgartner H. Helv. Chim. Acta 83 (2000) 539
21. Zhou Y., Linden A., and Heimgartner H. Helv. Chim. Acta 83 (2000) 1576
22. Atanassov P.K., Zhou Y., Linden A., and Heimgartner H. Helv. Chim. Acta 85 (2002) 1102
23. Atanassov P.K., Linden A., and Heimgartner H. Heterocycles 61 (2003) 569
24. Atanassov P.K., Linden A., and Heimgartner H. Helv. Chim. Acta 86 (2003) 3235
25. Atanassov P.K., Linden A., and Heimgartner H. Heterocycles 62 (2004) 521
26. Atanassov P.K., Linden A., and Heimgartner H. Helv. Chim. Acta 87 (2004) 1452
27. Atanassov P.K., Linden A., and Heimgartner H. Helv. Chim. Acta 87 (2004) 1873
28. Sommen G.L., Linden A., and Heimgartner H. Helv. Chim. Acta 88 (2005) 766
29. Sommen G.L., Linden A., and Heimgartner H. Eur. J. Org. Chem. 14 (2005) 3128
30. Sommen G.L., Linden A., and Heimgartner H. Heterocycles 65 (2005) 1903
31. Sommen G.L., Linden A., and Heimgartner H. Tetrahedron Lett. 46 (2005) 6723
32. G. L. Sommen, A. Linden, and H. Heimgartner, in preparation.
33. Witczak Z.J. Tetrahedron 41 (1985) 4781
34. Stec W.J., Lesiak K., and Sudol M. Synthesis (1975) 785
35. Sukata K. J. Org. Chem. 54 (1989) 2015
36. Petrov M.L., and Zmitrovich N.I. Russ. J. Gen. Chem. 69 (1999) 245
37. 33.
38. A. Alizadeh, Helv. Chim. Acta, 2005, in press.
39. Svanholm U. Acta. Chem. Scand. 26 (1972) 459
40. DE 2063575 (Chem. Abstr., 1971, 75, 76805). Brown J.C. Ger. Offen. (1971)
41. DE 2162855 (Chem. Abstr., 1972, 77, 140086). Brown J.C., Fry D.J., and Keogh P.J. Ger. Offen. (1972)
42. Korotkikh N.I., Rayenko G.F., Shvaika O.P., Pekhtereva T.M., Cowley A.H., Jones J.N., and Macdonald C.L.B. J. Org. Chem. 68 (2003) 5762
43. Enders D., Breuer K., Kallfass U., and Balensiefer T. Synthesis 8 (2003) 1292
44. Enders D., Breuer K., Runsink J., and Teles J.H. Liebigs Ann. (1996) 2019
45. Bocian W., Jazwinski J., and Stefaniak L. Pol. J. Chem. 69 (1995) 85
46. Lazaris A.Y., and Egorochkin A.N. Izv. Akad. Nauk. SSSR, Ser. Khim. 5 (1976) 1191
47. Filgueiras de Athayde-Filho P., Simas A.M., Cruz Goncalvez S.M., and Miller J. Phosphorus, Sulfur, Silicon & Rel. Elem. 161 (2000) 115
48. Barton D.H.R., Parekh S.I., Tajbakhsh M., Theodorakis E.A., and Tse C.-L. Tetrahedron 50 (1994) 639
49. Bakhsh M.T., Behshtiha Y.S., and Heravi M.M. J. Chem. Soc. Pakistan 18 (1996) 159
50. 44
51. Dembinski R. Eur. J. Org. Chem. 13 (2004) 2763
52. Arnold L.D., Assil H.I., and Vederas J.C. J. Am. Chem. Soc. 111 (1989) 3973
53. Johnson C.K. ORTEPII, Report ORNL-5138 (1976), Oak Ridge National Laboratory, Oak Ridge, Tennessee
54. Bittner S., Assaf Y., Krief P., Pomerantz M., Ziemnicka B.T., and Smith C.G. J. Org. Chem. 50 (1985) 1712
55. Mukaiyama T. Angew. Chem., Int. Ed. Engl. 15 (1976) 94
56. Mitsunobu O. Synthesis 1 (1981)
57. Fauduet H., and Burgada R. C.R. Acad. Sci. Ser. C 291 (1980) 81
58. Von Itzstein M., and Jenkins I.D. J. Chem. Soc., Perkin Trans. 1 (1986) 437
59. Camp D., and Jenkins I.D. J. Org. Chem. 54 (1989) 3049
60. Von Itzstein M., and Jenkins I.D. Aust. J. Chem. 36 (1983) 557
61. Niclas H.-J., and Martin D. Tetrahedron Lett. 42 (1978) 4031
62. Hughes D.L. Org. Reactions 42 (1992) 335
63. CCDC-279972 contains the supplementary crystallographic data for compound 7e. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
64. Hooft R. KappaCCD Collect Software (1999), Nonius BV, Delft, The Netherlands
65. Part A. Otwinowski Z., and Minor W. In: Carter Jr. C.W., and Sweet R.M. (Eds). Methods in Enzymology, Vol. 276, Macromolecular Crystallography (1997), Academic Press, New York 307
66. Blessing R.H. Acta Crystallogr., Sect A 51 (1995) 33
67. Sheldrick G.M. SHELXS97, Program for the Solution of Crystal Structures (1997), University of Göttingen, Germany
68. Vol. C Table 6.1.1.1. Maslen E.N., Fox A.G., and O'Keefe M.A. In: Wilson A.J.C. (Ed). International Tables for Crystallography (1992), Kluwer Academic Publishers, Dordrecht 477
69. Stewart R.F., Davidson E.R., and Simpson W.T. J. Chem. Phys. 42 (1965) 3175
70. Ibers J.A., and Hamilton W.C. Acta Crystallogr. 17 (1964) 781
71. Table 4.2.6.8. Creagh D.C., and McAuley W.J. In: Wilson A.J.C. (Ed). International Tables for Crystallography Vol. C (1992), Kluwer Academic Publishers, Dordrecht 219
72. Table 4.2.4.3. Creagh D.C., and Hubbell J.H. In: Wilson A.J.C. (Ed). International Tables for Crystallography Vol. C (1992), Kluwer Academic Publishers, Dordrecht 200
73. Sheldrick G.M. SHELXL97, Program for the Refinement of Crystal Structures (1997), University of Göttingen, Germany