Δ-1,3,4-Telluradiazolines, a novel tellurium containing heterocycle: One-pot synthesis, structure, and reactivity

Tetrahedron

Volumn 53, Issue 24, 1997, Pages 8137-8148

  Minoura, Mao ^a,b   Kawashima, Takayuki ^a   Tokitoh, Norihiro ^a   Okazaki, Renji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOTELLURIUM DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; IN VITRO STUDY; PHOTOLYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; TEMPERATURE; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY CRYSTALLOGRAPHY;

EID: 0030975092     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00498-5     Document Type: Article

References (58)

1. Uemura, S. Yuki Gosei Kagaku Kyokai Shi 1983, 41, 804-813; Engman, L. Acc. Chem. Res. 1985, 18, 274-279; Petragnani, N.; Comasseto, J. V. Synthesis 1986, 1-30; Suzuki, H. Yuki Gosei Kagaku Kyokai Shi 1987, 45, 603-615; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 793-812; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 897-919; Petragnani, N. Tellurium in Organic Synthsis; Academic Press: New York, 1994.
2. Uemura, S. Yuki Gosei Kagaku Kyokai Shi 1983, 41, 804-813; Engman, L. Acc. Chem. Res. 1985, 18, 274-279; Petragnani, N.; Comasseto, J. V. Synthesis 1986, 1-30; Suzuki, H. Yuki Gosei Kagaku Kyokai Shi 1987, 45, 603-615; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 793-812; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 897-919; Petragnani, N. Tellurium in Organic Synthsis; Academic Press: New York, 1994.
3. Uemura, S. Yuki Gosei Kagaku Kyokai Shi 1983, 41, 804-813; Engman, L. Acc. Chem. Res. 1985, 18, 274-279; Petragnani, N.; Comasseto, J. V. Synthesis 1986, 1-30; Suzuki, H. Yuki Gosei Kagaku Kyokai Shi 1987, 45, 603-615; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 793-812; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 897-919; Petragnani, N. Tellurium in Organic Synthsis; Academic Press: New York, 1994.
4. Uemura, S. Yuki Gosei Kagaku Kyokai Shi 1983, 41, 804-813; Engman, L. Acc. Chem. Res. 1985, 18, 274-279; Petragnani, N.; Comasseto, J. V. Synthesis 1986, 1-30; Suzuki, H. Yuki Gosei Kagaku Kyokai Shi 1987, 45, 603-615; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 793-812; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 897-919; Petragnani, N. Tellurium in Organic Synthsis; Academic Press: New York, 1994.
5. Uemura, S. Yuki Gosei Kagaku Kyokai Shi 1983, 41, 804-813; Engman, L. Acc. Chem. Res. 1985, 18, 274-279; Petragnani, N.; Comasseto, J. V. Synthesis 1986, 1-30; Suzuki, H. Yuki Gosei Kagaku Kyokai Shi 1987, 45, 603-615; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 793-812; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 897-919; Petragnani, N. Tellurium in Organic Synthsis; Academic Press: New York, 1994.
6. Uemura, S. Yuki Gosei Kagaku Kyokai Shi 1983, 41, 804-813; Engman, L. Acc. Chem. Res. 1985, 18, 274-279; Petragnani, N.; Comasseto, J. V. Synthesis 1986, 1-30; Suzuki, H. Yuki Gosei Kagaku Kyokai Shi 1987, 45, 603-615; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 793-812; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 897-919; Petragnani, N. Tellurium in Organic Synthsis; Academic Press: New York, 1994.
7. Uemura, S. Yuki Gosei Kagaku Kyokai Shi 1983, 41, 804-813; Engman, L. Acc. Chem. Res. 1985, 18, 274-279; Petragnani, N.; Comasseto, J. V. Synthesis 1986, 1-30; Suzuki, H. Yuki Gosei Kagaku Kyokai Shi 1987, 45, 603-615; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 793-812; Petragnani, N.; Comasseto, J. V. Synthesis 1991, 897-919; Petragnani, N. Tellurium in Organic Synthsis; Academic Press: New York, 1994.
8. Zingaro, R. A.; Irgolic, K. In Tellurium; Cooper, W. C. Ed.; Von Nostrand Reinhold: New York, 1971; pp 184-279; Irgolic, K. Y. In Houben-Weyl, Methods of Organic Chemistry; Klamann, D. Ed.; Georg Thieme: Stuttgart, 1990; Vol. E 12b; Sadekov, I. D.; Maksimenko, A. A.; Minkin, V. I. Sulfur Reports 1990, 9, 359-398; Chivers, T. J. Chem. Soc., Dalton Trans. 1996, 1185-1194.
9. Zingaro, R. A.; Irgolic, K. In Tellurium; Cooper, W. C. Ed.; Von Nostrand Reinhold: New York, 1971; pp 184-279; Irgolic, K. Y. In Houben-Weyl, Methods of Organic Chemistry; Klamann, D. Ed.; Georg Thieme: Stuttgart, 1990; Vol. E 12b; Sadekov, I. D.; Maksimenko, A. A.; Minkin, V. I. Sulfur Reports 1990, 9, 359-398; Chivers, T. J. Chem. Soc., Dalton Trans. 1996, 1185-1194.
10. Zingaro, R. A.; Irgolic, K. In Tellurium; Cooper, W. C. Ed.; Von Nostrand Reinhold: New York, 1971; pp 184-279; Irgolic, K. Y. In Houben-Weyl, Methods of Organic Chemistry; Klamann, D. Ed.; Georg Thieme: Stuttgart, 1990; Vol. E 12b; Sadekov, I. D.; Maksimenko, A. A.; Minkin, V. I. Sulfur Reports 1990, 9, 359-398; Chivers, T. J. Chem. Soc., Dalton Trans. 1996, 1185-1194.
11. Zingaro, R. A.; Irgolic, K. In Tellurium; Cooper, W. C. Ed.; Von Nostrand Reinhold: New York, 1971; pp 184-279; Irgolic, K. Y. In Houben-Weyl, Methods of Organic Chemistry; Klamann, D. Ed.; Georg Thieme: Stuttgart, 1990; Vol. E 12b; Sadekov, I. D.; Maksimenko, A. A.; Minkin, V. I. Sulfur Reports 1990, 9, 359-398; Chivers, T. J. Chem. Soc., Dalton Trans. 1996, 1185-1194.
12. Detty, M. R.; O'Regan, M. B. Tellurium-containing Heterocycles; John Wiley & Sons: New York, 1994; Renson, M. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S. and Rappoport, Z. Eds.; John Wiley & Sons: New York, 1986; Vol. 1; pp 421-461; Sadekov, I. D.; Minkin, V. I.; Garnovskii, A. D. Sulfur Reports 1985, 5, 63-115; Sadekov, I. D.; Abakarov, G. M.; Sadekova, Y. I.; Minkin, V. I. Sulfur Reports 1986, 6, 15-69; Sadekov, I. D.; Minkin, V. I. In Advances in Heterocyclic Chemistry; Katritzky, A. R. Ed.; Academic Press: New York, 1994; Vol. 58; pp 47-121.
13. Detty, M. R.; O'Regan, M. B. Tellurium-containing Heterocycles; John Wiley & Sons: New York, 1994; Renson, M. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S. and Rappoport, Z. Eds.; John Wiley & Sons: New York, 1986; Vol. 1; pp 421-461; Sadekov, I. D.; Minkin, V. I.; Garnovskii, A. D. Sulfur Reports 1985, 5, 63-115; Sadekov, I. D.; Abakarov, G. M.; Sadekova, Y. I.; Minkin, V. I. Sulfur Reports 1986, 6, 15-69; Sadekov, I. D.; Minkin, V. I. In Advances in Heterocyclic Chemistry; Katritzky, A. R. Ed.; Academic Press: New York, 1994; Vol. 58; pp 47-121.
14. Detty, M. R.; O'Regan, M. B. Tellurium-containing Heterocycles; John Wiley & Sons: New York, 1994; Renson, M. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S. and Rappoport, Z. Eds.; John Wiley & Sons: New York, 1986; Vol. 1; pp 421-461; Sadekov, I. D.; Minkin, V. I.; Garnovskii, A. D. Sulfur Reports 1985, 5, 63-115; Sadekov, I. D.; Abakarov, G. M.; Sadekova, Y. I.; Minkin, V. I. Sulfur Reports 1986, 6, 15-69; Sadekov, I. D.; Minkin, V. I. In Advances in Heterocyclic Chemistry; Katritzky, A. R. Ed.; Academic Press: New York, 1994; Vol. 58; pp 47-121.
15. Detty, M. R.; O'Regan, M. B. Tellurium-containing Heterocycles; John Wiley & Sons: New York, 1994; Renson, M. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S. and Rappoport, Z. Eds.; John Wiley & Sons: New York, 1986; Vol. 1; pp 421-461; Sadekov, I. D.; Minkin, V. I.; Garnovskii, A. D. Sulfur Reports 1985, 5, 63-115; Sadekov, I. D.; Abakarov, G. M.; Sadekova, Y. I.; Minkin, V. I. Sulfur Reports 1986, 6, 15-69; Sadekov, I. D.; Minkin, V. I. In Advances in Heterocyclic Chemistry; Katritzky, A. R. Ed.; Academic Press: New York, 1994; Vol. 58; pp 47-121.
16. Detty, M. R.; O'Regan, M. B. Tellurium-containing Heterocycles; John Wiley & Sons: New York, 1994; Renson, M. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S. and Rappoport, Z. Eds.; John Wiley & Sons: New York, 1986; Vol. 1; pp 421-461; Sadekov, I. D.; Minkin, V. I.; Garnovskii, A. D. Sulfur Reports 1985, 5, 63-115; Sadekov, I. D.; Abakarov, G. M.; Sadekova, Y. I.; Minkin, V. I. Sulfur Reports 1986, 6, 15-69; Sadekov, I. D.; Minkin, V. I. In Advances in Heterocyclic Chemistry; Katritzky, A. R. Ed.; Academic Press: New York, 1994; Vol. 58; pp 47-121.
17. Boger, D. L.; Weinreb, D. L. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: New York, 1991; Metzner, P. Synthesis 1992, 1185-1199; Bryce, M. R.; Bechere, J.; Falt-Hansen, B. In Advances in Heterocyclic Chemistry; Katritzky, A. R. Ed.; Academic Press: New York, 1993; Vol. 55; pp 1-29.
18. Boger, D. L.; Weinreb, D. L. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: New York, 1991; Metzner, P. Synthesis 1992, 1185-1199; Bryce, M. R.; Bechere, J.; Falt-Hansen, B. In Advances in Heterocyclic Chemistry; Katritzky, A. R. Ed.; Academic Press: New York, 1993; Vol. 55; pp 1-29.
19. Boger, D. L.; Weinreb, D. L. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: New York, 1991; Metzner, P. Synthesis 1992, 1185-1199; Bryce, M. R.; Bechere, J.; Falt-Hansen, B. In Advances in Heterocyclic Chemistry; Katritzky, A. R. Ed.; Academic Press: New York, 1993; Vol. 55; pp 1-29.
20. a) Barton, D. H. R.; Willis, B. J. J. Chem. Soc., Perkin Trans. 1 1972, 305-310;
21. b) Barton, D. H. R.; Guziec, F. S., Jr.; Shahak, I. J. Chem. Soc., Perkin Trans. 1 1974, 1794-1799;
22. c) Krebs, W.; Rüger, W.; Nickel, W.-U. Tetrahedron Lett. 1981, 22, 4937-4940;
23. d) Loerzer, T.; Gerke, R.; Lüttke, W. Tetrahedron Lett. 1983, 24, 5861-5864;
24. e) Krebs, W.; Rüger, W.; Ziegenhagen, B.; Hebold, M.; Hardtke, I.; Müller, R.; Schütz, M.; Wietzke, M.; Wilke, M. Chem. Ber. 1984, 117, 277-309;
25. f) Krebs, A.; Kaletta, B.; Nickel, W.-U.; Rüger, W.; Tikwe, L. Teterahedron 1986, 42, 1693-1702.
26. a) Back, T. G.; Barton, D. H. R.; Britten-Kelly, M. B. R.; Guziec, F. S., Jr. J. Chem. Soc., Chem. Commun. 1975, 539;
27. b) Back, T. G.; Barton, D. H. R.; Britten-Kelly, M. B. R.; Guziec, F. S., Jr. J. Chem. Soc., Perkin Trans. 1 1976, 2079-2089;
28. c) Guziec, F. S., Jr.; Murphy, C. J. J. Org. Chem. 1980, 45, 2890-2893;
29. d) Cullen, E. R.; Guziec, F. S., Jr.; Hollander, I.; Murphy, C. J. Tetrahedron Lett. 1981, 22, 4563-4566;
30. e) Cullen, E. R.; Guziec, F. S., Jr.; Murphy, C. J. J. Org. Chem. 1982, 47, 3563-3566;
31. f) Guziec, F. S., Jr.; SanFilippo, L. J.; Murphy, C. J.; Moustakis, C. A.; Cullen, E. R. Tetrahedron 1985, 41, 4843-4852;
32. g) Guziec, F. S., Jr; Murphy, C. J.; Cullen, E. W. J. Chem. Soc., Perkin Trans. 1 1985, 107-113;
33. h) Guziec, F. S., Jr.; SanFilippo, L. J. J. Org. Chem. 1991, 56, 3178-3181;
34. i) Brooks, P. R.; Bishop, R.; Craig, D. C.; Scudder, M. L. J. Org. Chem. 1993, 58, 5900-5906.
35. Guziec, F. S., Jr.; SanFilippo, L. J. Tetrahedron 1988, 44, 6241-6285.
36. Minoura, M.; Kawashima, T.; Okazaki, R. J. Am. Chem. Soc. 1993, 115, 7019-7020.
37. Minoura, M.; Kawashima, T.; Tokitoh, N.; Okazaki, R. J. Chem. Soc., Chem. Commun. 1996, 123-124.
38. A part of the present work was preliminarily reported. Okazaki, R.; Minoura, M.; Kawashima, T. Chem. Lett. 1993, 1047-1048; Minoura, M.; Kawashima, T.; Okazaki, R. Tetrahedron Lett. in press.
39. A part of the present work was preliminarily reported. Okazaki, R.; Minoura, M.; Kawashima, T. Chem. Lett. 1993, 1047-1048; Minoura, M.; Kawashima, T.; Okazaki, R. Tetrahedron Lett. in press.
40. Okazaki, R.; Inoue, K.; Inamoto, N. Tetrahedron Lett. 1979, 38, 3673-3676; Okazaki, R.; Inoue, K.; Inamoto, N. Bull. Chem. Soc. Jpn. 1981, 54, 3541-3545.
41. Okazaki, R.; Inoue, K.; Inamoto, N. Tetrahedron Lett. 1979, 38, 3673-3676; Okazaki, R.; Inoue, K.; Inamoto, N. Bull. Chem. Soc. Jpn. 1981, 54, 3541-3545.
42. Okazaki, R.; Ishii, A.; Inamoto, N. J. Chem. Soc., Chem. Commun. 1983, 1429-1430; Guziec, F. S., Jr.; Moustakis, C. A. J. Org. Chem. 1984, 49, 189-191; Ishii, A.; Okazaki, R.; Inamoto, N. Bull. Chem. Soc. Jpn. 1988, 61, 861-867.
43. Okazaki, R.; Ishii, A.; Inamoto, N. J. Chem. Soc., Chem. Commun. 1983, 1429-1430; Guziec, F. S., Jr.; Moustakis, C. A. J. Org. Chem. 1984, 49, 189-191; Ishii, A.; Okazaki, R.; Inamoto, N. Bull. Chem. Soc. Jpn. 1988, 61, 861-867.
44. Okazaki, R.; Ishii, A.; Inamoto, N. J. Chem. Soc., Chem. Commun. 1983, 1429-1430; Guziec, F. S., Jr.; Moustakis, C. A. J. Org. Chem. 1984, 49, 189-191; Ishii, A.; Okazaki, R.; Inamoto, N. Bull. Chem. Soc. Jpn. 1988, 61, 861-867.
45. Greenwood, N. N.; Earnshaw, A. Chemistry of The Elements; Pergamon Press: Oxford, 1984; pp 882-919.
46. Aynsley, E. E. J. Chem. Soc. 1953, 3016-3019.
47. McFarlane, H. C. E.; McFarlane, W. In Multinuclear NMR; Mason, J. Ed.; Plenum Press: New York, 1987; pp 417-435.
48. Minoura, M.; Kawashima, T.; Okazaki, R. Chem. Lett. 1994, 1691-1692.
49. Chivers, T.; Gao, X.; Parvez, M. Inorg. Chem. 1996, 35, 9-15; Kirsch, G.; Christianes, L. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S. Ed.; John Wiley & Sons: New York, 1987; Vol. 2; pp 421-461.
50. Chivers, T.; Gao, X.; Parvez, M. Inorg. Chem. 1996, 35, 9-15; Kirsch, G.; Christianes, L. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S. Ed.; John Wiley & Sons: New York, 1987; Vol. 2; pp 421-461.
51. Campsteyn, H.; Dupont, L.; Lamotte-Brasseur, J.; Vermeire, M. J. Heterocyclic Chem. 1978, 15, 745-748.
52. Bertini, V.; Dapporto, P.; Lucchesini, F.; Sega, A.; DeMunno, A. Acta. Cryst. Sect. C 1984, C40, 653-656.
53. Bergman, J.; Engman, L. J. Am. Chem. Soc. 1981, 103, 2715-2718.
54. Paul, R. C.; Arneja, A.; Narula, S. P. Inorg. Nucl. Chem. Lett. 1969, 5, 1013-1015.
55. Horan, J. E.; Schiessler, R. W. Org. Synth. 1961, 41, 1013-1015.
56. Langhals, E.; Langhals, H. Tetrahedron Lett. 1990, 31, 859-862.
57. Millard, A. A.; Rathke, M. W. J. Org. Chem. 1978, 43, 1834-1835.
58. Starr, J. E.; Eastman, R. H. J. Org. Chem. 1966, 31, 1393-1402.