Selenium-containing heterocycles from isoselenocyanates: Use of hydrazine for the synthesis of 1,3,4-selenadiazine derivatives

Helvetica Chimica Acta

Volumn 89, Issue 7, 2006, Pages 1322-1329

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

^a UNIVERSITY OF ZURICH   (Switzerland)

^b LONZA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; HYDRATES; SELENIUM; SYNTHESIS (CHEMICAL);

ARYL ISOSELENOCYANATES; HETEROCYCLES; HYDRAZINE HYDRATE;

HYDRAZINE;

(3,6 DIHYDRO 5 PHENYL 2H [1,3,4]SELENADIAZIN 2 YLIDENE)(4 METHOXYPHENYL)AMINE; (3,6 DIHYDRO 5 PHENYL 2H [1,3,4]SELENADIAZIN 2 YLIDENE)(PHENYL)AMINE; (4 BROMOPHENYL)(3,6 DIHYDRO 5 PHENYL 2H [1,3,4]SELENADIAZIN 2 YLIDEN)AMINE; (4 BROMOPHENYL)[2 (4 BROMOPHENYL) 3,6 DIHYDRO 2H [1,3,4]SELENADIAZIN 2 YLIDEN)AMINE; (4 CHLOROPHENYL)(3,6 DIHYDRO 5 PHENYL 2H [1,3,4]SELENADIAZIN 2 YLIDEN)AMINE; 1,3,4 SELENADIAZINE DERIVATIVE; [5 (4 BROMOPHENYL) 3,6 DIHYDRO 2H [1,3,4]SELENADIAZIN 2 YLIDENE](4 METHYLPHENYL)AMINE; AMINE; CYANIC ACID DERIVATIVE; HALIDE; HETEROCYCLIC COMPOUND; HYDRAZINE; ISOSELENOCYANATE DERIVATIVE; PHENYL HALIDE DERIVATIVE; SELENIUM; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 33746930653     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200690131     Document Type: Article

References (64)

1. M. Koketsu, H. Ishihara, Curr. Org. Chem. 2003, 7, 175.
2. M. Morvan, G. Nadler, R. G. Zimmermann, J. Heterocycl. Chem. 1991, 28, 1365.
3. J. Sihor, W.-D. Pfeiffer, A. Hetzheim, P. Pazdera, Scripta Chem. 1998, 27-28, 33
4. (Chem. Absrr. 1999, 132, 23022).
5. J. Liebscher, H. Hartmann, Ger. Pat., 1977, DD126309 (Chem. Abstr. 1978, 88, 62425);
6. W.-D. Pfeiffer, H. Rossberg, E. Bulka, Ger. Pat., 1983, DD203541 (Chem. Abstr. 1984, 100, 156644);
7. W.-D. Pfeiffer, E. Bulka. Ger. Pat., 1986, DD234678 (Chem. Abstr. 1986, 105, 226667);
8. W.-D. Pfeiffer, E. Bulka, Ger. Pat., 1991, DD290012; (Chem. Abstr. 1991, 115, 183376).
9. I. Shibuya, H. Nakanishi. Bull. Chem. Soc. Jpn. 1987, 60, 2686;
10. R. N. Butler, A. Fox, J. Chem. Soc., Perkin Trans. 1 2001, 394.
11. H. G. Grant, L. A. Summers, Z. Naturforsch., B: Anorg. Chem. 1978, 33, 118.
12. A. Gieren, V. Lamm, R. C. Haddon, M. L. Kaplan, J. Am. Chem. Soc. 1980, 102, 5070;
13. J. P. Boutique, J. Riga, J. J. Verbist, J. Delhalle, J. G. Fripiat, J. M. Andre, R. C. Haddon, M. L. Kaplan, J. Am. Chem. Soc. 1982, 104, 2691;
14. A. Haas, E. Hoppmann, V. M. Karpov, V. E. Platonov, M. M. Shakirov, J. Fluorine Chem. 2000, 102, 313.
15. M.-C. Forest, P. Lahouratate, M. Martin, G. Nadler, M. J. Quiniou, R. G. Zimmermann, J. Med. Chem. 1992, 35, 163.
16. [9| W.-D. Pfeiffer, E. Bulka, Ger. Pat., 1990, DD281582 (Chem. Abstr. 1991, 114, 185571).
17. I. Shibuya, H. Nakanishi, Jap. Pat., 1987, JP62106088 (Chem. Abstr. 1988, 108, 221705).
18. E. Bulka. Chem. Ser. 1975, 8A, 39
19. (Chem. Abstr. 1976, 85, 21162).
20. B. Marcewicz-Rojewska, S. Bilinski, Acta Pol. Pharm. 1980, 37, 169;
21. S. Bilinski, L. Bielak, J. Chmielewski, B. Marcewicz-Rojewska, I. Musik. Acta Pol. Pharm. 1989, 46, 343.
22. V. A. Bobylev, M. L. Petrov, V. N. Chistokletov, A. A. Petrov, J. Org. Chem. USSR 1982, 18, 200;
23. M. L. Petrov, M. A. Abramov, V. A. Galishev, A. A. Petrov, J. Org. Chem. USSR 1989, 25, 181.
24. H. Rossberg, W.-D. Pfeiffer, E. Bulka, Wiss. Z. Ernst-Moritz-Arndt-Univ. Greifswald, Math.-nat.-wiss. Reihe, 1985, 34, 75:
25. W.-D. Pfeiffer, J. Buhrow, E. Bulka, Wiss. Z. Ernst-Moritz-Arndt-Univ. Greifswald, Math.-nat.wiss. Reihe, 1988, 37, 38;
26. W.-D. Pfeiffer, E. Bulka, Chem. Ztg. 1991, 115, 361:
27. T. Jira, W.-D. Pfeiffer, K. Lachmann, U. Epperlein, Pharmazie 1994, 49, 401;
28. W.-D. Pfeiffer, H. Rossberg, Pharmazie 1993, 48, 732;
29. T. Jira, A. Stelzer, W.-D. Pfeiffer, C. Schopplich, S. Siegert, M. Kindermann, Pharmazie 1997, 52, 831.
30. H. Schubert, J. Bleichert, Z. Chem. 1963, 9, 349;
31. K. Szulzewski, W.-D. Pfeiffer, E. Bulka, H. Rossberg, B. Schulz, Acta Chem. Scand. 1993, 47, 302.
32. Y. V. Zachinyaev, A. I. Bobrov. Ukr. Khim. Zh. 1988, 54, 538
33. (Chem. Abstr. 1989, 110, 212778);
34. Y. V. Zachinyaev, A. I. Bobrov, A. I. Ginak. Rev. Roum. Chim. 1989, 34, 901
35. (Chem. Abstr. 1990, 112, 77132).
36. Y. Zhou, H. Heimgartner, Helv. Chim. Acta 2000, 83, 539.
37. Y. Zhou, A. Linden, H. Heimgartner. Helv. Chim. Acta 2000, 83, 1576.
38. P. K. Atanassov, Y. Zhou, A. Linden, H. Heimgartner. Helv. Chim. Acta 2002, 85, 1102.
39. P. K. Atanassov, A. Linden, H. Heimgartner, Heterocycles 2003, 61, 569.
40. P. K. Atanassov, A. Linden, H. Heimgartner, Heterocycles 2004, 62, 521.
41. P. K. Atanassov, A. Linden, H. Heimgartner, Helv. Chim. Acta 2004, 87, 1452.
42. P. K. Atanassov, A. Linden, H. Heimgartner, Helv. Chim. Acta 2004, 87, 1873.
43. P. K. Atanassov, A. Linden, H. Heimgartner, J. Sulfur Chem. 2006, 27, 181.
44. G. L. Sommen, A. Linden, H. Heimgartner, Helv. Chim. Acta 2005, 88, 766.
45. G. L. Sommen, A. Linden, H. Heimgartner, Eur. J. Org. Chem. 2005, 128.
46. G. L. Sommen, A. Linden, H. Heimgartner, Tetrahedron 2006, 62, 3344.
47. G. L. Sommen, A. Linden, H. Heimgartner, Tetrahedron Lett. 2005, 46, 6723.
48. D. H. R. Barton, S. I. Parekh, M. Tajbakhsh, E. A. Theodorakis, C.-L. Tse, Tetrahedron 1994, 50, 639;
49. M. T. Bakhsh, Y. S. Behshtiha, M. M. Heravi J. Chem. Soc. Pakistan 1996, 18, 159.
50. C. K. Johnson, 'ORTEP II', Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
51. J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang. Angew. Chem., Int. Ed. 1995, 34, 1555.
52. J. E. Baldwin. J. Chem. Soc., Chem. Commun. 1976, 734.
53. G. L. Sommen, A. Linden, H. Heimgartner. Heterocycles 2005, 65, 1903.
54. F. Favero, G. L. Sommen, A. Linden, H. Heimgartner, Heterocycles 2006, 67, 749.
55. R. Hooft, KappaCCD Collect Software, Nonius BV, Delft. The Netherlands, 1999.
56. Z. Otwinowski, W. Minor, in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography', Part A, Eds. C. W. Carter Jr., R. M. Sweet. Academic Press, New York, 1997, p. 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.