Selenium-containing heterocycles from isoselenocyanates: Cycloaddition of carbodiimides to selenazetidines

Helvetica Chimica Acta

Volumn 88, Issue 4, 2005, Pages 766-773

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

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBODIIMIDES; CYCLOADDITION; ISOSELENOCYANATES; SELENAZETIDINES;

ADDITION REACTIONS; AROMATIC COMPOUNDS; MOLECULAR STRUCTURE; X RAY CRYSTALLOGRAPHY;

SELENIUM;

1,3 SELENAZETIDINE 2,4 DIIMINE; 4 BROMO N [3 CYCLOHEXYL 4 (CYCLOHEXYLIMINO) 1,3 SELENAZETIDIN 2 YLIDENE]BENZENAMINE; 4 BROMO N [3 ISOPROPYL 4 (ISOPROPYLIMINO) 1,3 SELENAZETIDIN 2 YLIDENE]BENZENAMINE; 4 CHLORO N 3 [ISOPROPYL 4 (ISOPROPYLIMINO) 1,3 SELENAZETIDIN 2 YLIDENE]BENZENAMINE; 4 CHLORO N [3 CYCLOHEXYL 4 (CYCLOHEXYLIMINO) 1,3 SELENAZETIDIN 2 YLIDENE]BENZENAMINE; AZETIDINE DERIVATIVE; CYANAMIDE; CYANIC ACID DERIVATIVE; CYCLOHEXYL N [3 CYCLOHEXYL 4 (CYCLOHEXYLIMINO) 1,3 SELENAZETIDIN 2 YLIDENE]BENZENAMINE; CYCLOHEXYL N [3 ISOPROPYL 4 (ISOPROPYLIMINO) 1,3 SELENAZETIDIN 2 YLIDENE]BENZENAMINE; HETEROCYCLIC COMPOUND; HEXANE; ISOSELENOCYANATE DERIVATIVE; N [3 CYCLOHEXYL 4 (CYCLOHEXYLIMINO) 1,3 SELENAZETIDIN 2 YLIDENE]BENZENAMINE; N [3 ISOPROPYL 4 (ISOPROPYLIMINO) 1,3 SELENAZETIDIN 2 YLIDENE]BENZENAMINE; SELENAZETIDINE DERIVATIVE; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; CRYSTAL STRUCTURE; CYCLOADDITION; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 18744397523     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200590053     Document Type: Article

References (64)

1. D. L. Klayman, W. H. H. Günther, 'Organic Selenium Compounds: Their Chemistry and Biology', John Wiley & Sons, New York, 1973, p. 579 and 629.
2. C. Paulmier, 'Selenium Reagents and Intermediates in Organic Synthesis', Pergamon Press, Oxford, 1986, p. 70.
3. M. Renson, 'The Chemistry of Organic Selenium and Tellurium Compounds', Vol. 1, Eds. S. Patai, Z. Rappoport, John Wiley & Sons, New York, 1986, p. 399.
4. V. P. Litvinov, V. D. Dyachenko, Russ. Chem. Rev. 1997, 66, 923.
5. T. Wirth, Tetrahedron 1999, 55, 1.
6. 'Organoselenium Chemistry, a Practical Approach', Ed. T. G. Back, Oxford University Press, Oxford, 1999.
7. H. J. Reich, in 'Topics in Current Chemistry: Organoselenium Chemistry, Modern Development in Organic Synthesis', Vol. 208, Ed. T. Wirth, Springer Verlag, Berlin, 2000.
8. R. A. Passwaters, 'Selenium as Food & Medicine', Pivot Original Press, New Canaan, 1980.
9. 'Selenium in Biology and Medicine', Ed. A. Wengel, Springer Verlag, Berlin, 1989.
10. R. F. Burk, 'Selenium in Biology and Human Health', Springer Verlag, New York, 1994.
11. S. Janzsu, G. Hoppert, J. Shodiere, J.-C. Yerdon, to Jpn. Kokai Tokkyo Koho, Jap. Pat. 11140067, 1999.
12. Y. Xu, E. T. Kool, J. Am. Chem. Soc. 2000, 122, 9040.
13. Y. Ogasawara, G. Lacourciere, T. C. Stadtman, Proc. Natl. Acad. Sci. USA 2001, 98, 9494.
14. H. E. Ganther, Bioorg. Med. Chem. 2001, 9, 1459.
15. G. Mugesh, W.-W. Du Mont, H. Sies, Chem. Rev. 2001, 101, 2125.
16. S. W. May, Exp. Opin. Invest. Drugs 2002, 11, 1261.
17. E. V. Ratushnaya, Y. I. Kirova, M. A. Suchkov, B. I. Drevko, V. B. Borodulin, Pharm. Chem. J. 2002, 36, 652.
18. C. Jacob, G. Giles, F. Fry, U.S. Pat. WO 2004047925, 2004.
19. R. J. Shamberger, 'Biochemistry of Selenium', Plenum Press, New York, 1983.
20. D. L. Hatfield, 'Selenium. Its Molecular Biology and Role in Human Health', Kluwer Academic Publishers, Boston, 2001.
21. K. El-Bayoumy, R. Sinha, Mutat. Res. 2004, 551, 181.
22. C. Ip, M. Birringer, E. Block, M. Kotrebai, J. F. Tyson, P. C. Uden, D. J. Lisk, J. Agric. Food Chem. 2000,48, 2062.
23. J. Lintschinger, N. Fuchs, J. Moser, D. Kuehnelt, W. Goessler, J. Agric. Food Chem. 2000, 48, 5362.
24. V. Poggi, A. Arcioni, P. Filippini, P. G. Pifferi, J. Agric. Food Chem. 2000, 48, 4749.
25. P. Ximenez-Embun, I. Alonso, Y. Madrid-Albarran, C. Camara, J. Agric. Food Chem. 2004, 52, 832.
26. D. B. Vickerman, J. T. Trumble, G. N. George, I. J. Pickering, H. Nichol, Environ. Sci. Technol. 2004, 38, 3581.
27. W. J. Stec, K. Lesiak, M. Sudol, Synthesis 1975, 12, 785.
28. Z. J. Witczak, Tetrahedron 1985, 41, 4781.
29. K. Sukata, J. Org. Chem. 1989, 54, 2015.
30. M. L. Petrov, N. I. Zmitrovich, Russ. J. Gen. Chem. 1999, 69, 245.
31. a) Y. Zhou, H. Heimgartner, Helv. Chim. Acta 2000, 83, 539;
32. b) Y. Zhou, A. Linden, H. Heimgartner, Helv. Chim. Acta 2000, 83, 1576;
33. c) P. K. Atanassov, Y. Zhou, A. Linden, H. Heimgartner, Helv. Chim. Acta 2002, 85, 1102.
34. a) P. K. Atanassov, A. Linden, H. Heimgartner, Helv. Chim. Acta 2003, 86, 3235;
35. b) P. K. Atanassov, A. Linden, H. Heimgartner, Heterocycles 2003, 61, 569;
36. c) P. K. Atanassov, A. Linden, H. Heimgartner, Heterocycles 2004, 62, 521;
37. d) P. K. Atanassov, A. Linden, H. Heimgartner, Helv. Chim. Acta 2004, 87, 1152;
38. e) P. K. Atanassov, A. Linden, H. Heimgartner, Helv. Chim. Acta 2004, 87, 1873.
39. D. H. R. Barton, S. I. Parekh, M. Tajbakhsh, E. A. Theodorakis, C.-L. Tse, Tetrahedron, 1994, 50, 639;
40. M. T. Bakhsh, Y. S. Behshtiha, M. M. Heravi, J. Chem. Soc. Pakistan 1996, 18, 159.
41. W. Manz, G. Gattow, Z. Anorg. Allg. Chem. 1994, 620, 151.
42. L. Henricksen, Int. J. Sulfur Chem. 1973, 8, 389.
43. H. Maeda, N. Kambe, N. Sonoda, S.-I. Fujiwara, T. Shin-ike, Tetrahedron 1997, 53, 13667.
44. C. Collard-Charon, R. Huls, M. Renson, Bull. Soc. Chim. Belg. 1962, 71, 541;
45. C. Collard-Charon, M. Renson, Bull. Soc. Chim. Belg. 1962, 71, 554;
46. K. A. Jensen, G. Felbert, C. T. Pedersen, U. Svanholm, Acta Chem. Scand. 1966, 20, 278.
47. M. Koketsu, N. Suzuki, H. Ishihara, J. Org. Chem. 1999, 64, 6473.
48. K. Rosenbaum, L. Beyer, R. Szargan, I. Uhlig, K. H. Hallmeier, J. Prakt. Chem. 1993, 335, 381.
49. N. Kano, Y. Daicho, N. Nakanishi, T. Kawasima, Org. Lett. 2001, 3, 691;
50. N. Kano, Y. Daicho, N. Nakanishi, T. Kawasima, Phosphorus, Sulfur Silicon Relat. Elem. 2001, 168, 259.
51. I. Ojima, K. Akiba, N. Inamoto, Bull. Chem. Soc. Jpn. 1973, 8, 2559.
52. M. Marchalin, J. Svetlik, A. Martvon, Coll. Czech. Chem. Commun. 1981, 46, 2557.
53. J. Bödeker, A. Köckritz, Z. Chem. 1982, 22, 140.
54. C. K. Johnson, 'ORTEP II', Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
55. R. Hooft, KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
56. Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307.
57. R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33.
58. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435.
59. a) E. N. Maslen, A. G. Fox, M. A. O'Keefe, in 'International Tables for Crystallography', Ed. A. J. C Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 6.1.1.1, p. 477;
60. b) D. C. Creagh, W. J. McAuley, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 4.2.6.8, p. 219;
61. c) D. C. Creagh, J. H. Hubbell, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 4.2.4.3, p. 200.
62. R. F. Stewart, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
63. J. A. Ibers, W. C. Hamilton, Acta Crystallogr. 1964, 17, 781.
64. G. M. Sheldrick, SHELXL97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.