Ring-Enlargement Reaction of 3-Alkyl-2-(N-cyanoimino)thiazolidine 1-Oxide: Formation of Novel 5,6-Dihydro-2H-1,2,4-thiadiazin-3(4H)-one Derivatives

Synlett

Volumn 1997, Issue 3, 1997, Pages 316-318

  Tanaka, Tetsuaki ^a   Takase, Wakako ^a   Fang, Xie ^a   Azuma, Tsutomu ^a   Uchida, Shuji ^b   Ishida, Toshimasa ^c   In, Yasuko ^c   Iwata, Chuzo ^a  

^a OSAKA UNIVERSITY   (Japan)

^b SETSUNAN UNIVERSITY   (Japan)

^c OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000573315     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-778     Document Type: Article

References (30)

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2. Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Heterocycles 1988, 27, 323-326; Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Synthesis 1988, 261-262; Iwata, C.; Fujimoto, M.; Okamoto, S.; Nishihara, C.; Sakae, M.; Katsurada, M.; Watanabe, M.; Kawakami, T.; Tanaka, T.; Imanishi, T. Heterocycles 1990, 31, 1601-1604; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Maeda, N.; Imanishi, T.; Tanaka, T. Heterocycles 1991, 32, 2471-2478; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Nakamoto, Y.; Sakae, M.; Katsurada, M.; Imanishi, T.; Tanaka, T. J. Chem. Soc., Chem. Commun. 1992, 1379-1381; Tanaka, T; Watanabe, M.; Nakamoto, Y.; Okuno, K.; Maekawa, K.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 2301-2302; Tanaka, T.; Nakamoto, Y.; Maekawa, K.; Watanabe, M.; Nishihara, C.; Iwata, C. Heterocycles 1996, 42, 265-272.
3. Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Heterocycles 1988, 27, 323-326; Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Synthesis 1988, 261-262; Iwata, C.; Fujimoto, M.; Okamoto, S.; Nishihara, C.; Sakae, M.; Katsurada, M.; Watanabe, M.; Kawakami, T.; Tanaka, T.; Imanishi, T. Heterocycles 1990, 31, 1601-1604; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Maeda, N.; Imanishi, T.; Tanaka, T. Heterocycles 1991, 32, 2471-2478; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Nakamoto, Y.; Sakae, M.; Katsurada, M.; Imanishi, T.; Tanaka, T. J. Chem. Soc., Chem. Commun. 1992, 1379-1381; Tanaka, T; Watanabe, M.; Nakamoto, Y.; Okuno, K.; Maekawa, K.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 2301-2302; Tanaka, T.; Nakamoto, Y.; Maekawa, K.; Watanabe, M.; Nishihara, C.; Iwata, C. Heterocycles 1996, 42, 265-272.
4. Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Heterocycles 1988, 27, 323-326; Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Synthesis 1988, 261-262; Iwata, C.; Fujimoto, M.; Okamoto, S.; Nishihara, C.; Sakae, M.; Katsurada, M.; Watanabe, M.; Kawakami, T.; Tanaka, T.; Imanishi, T. Heterocycles 1990, 31, 1601-1604; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Maeda, N.; Imanishi, T.; Tanaka, T. Heterocycles 1991, 32, 2471-2478; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Nakamoto, Y.; Sakae, M.; Katsurada, M.; Imanishi, T.; Tanaka, T. J. Chem. Soc., Chem. Commun. 1992, 1379-1381; Tanaka, T; Watanabe, M.; Nakamoto, Y.; Okuno, K.; Maekawa, K.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 2301-2302; Tanaka, T.; Nakamoto, Y.; Maekawa, K.; Watanabe, M.; Nishihara, C.; Iwata, C. Heterocycles 1996, 42, 265-272.
5. Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Heterocycles 1988, 27, 323-326; Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Synthesis 1988, 261-262; Iwata, C.; Fujimoto, M.; Okamoto, S.; Nishihara, C.; Sakae, M.; Katsurada, M.; Watanabe, M.; Kawakami, T.; Tanaka, T.; Imanishi, T. Heterocycles 1990, 31, 1601-1604; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Maeda, N.; Imanishi, T.; Tanaka, T. Heterocycles 1991, 32, 2471-2478; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Nakamoto, Y.; Sakae, M.; Katsurada, M.; Imanishi, T.; Tanaka, T. J. Chem. Soc., Chem. Commun. 1992, 1379-1381; Tanaka, T; Watanabe, M.; Nakamoto, Y.; Okuno, K.; Maekawa, K.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 2301-2302; Tanaka, T.; Nakamoto, Y.; Maekawa, K.; Watanabe, M.; Nishihara, C.; Iwata, C. Heterocycles 1996, 42, 265-272.
6. Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Heterocycles 1988, 27, 323-326; Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Synthesis 1988, 261-262; Iwata, C.; Fujimoto, M.; Okamoto, S.; Nishihara, C.; Sakae, M.; Katsurada, M.; Watanabe, M.; Kawakami, T.; Tanaka, T.; Imanishi, T. Heterocycles 1990, 31, 1601-1604; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Maeda, N.; Imanishi, T.; Tanaka, T. Heterocycles 1991, 32, 2471-2478; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Nakamoto, Y.; Sakae, M.; Katsurada, M.; Imanishi, T.; Tanaka, T. J. Chem. Soc., Chem. Commun. 1992, 1379-1381; Tanaka, T; Watanabe, M.; Nakamoto, Y.; Okuno, K.; Maekawa, K.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 2301-2302; Tanaka, T.; Nakamoto, Y.; Maekawa, K.; Watanabe, M.; Nishihara, C.; Iwata, C. Heterocycles 1996, 42, 265-272.
7. Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Heterocycles 1988, 27, 323-326; Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Synthesis 1988, 261-262; Iwata, C.; Fujimoto, M.; Okamoto, S.; Nishihara, C.; Sakae, M.; Katsurada, M.; Watanabe, M.; Kawakami, T.; Tanaka, T.; Imanishi, T. Heterocycles 1990, 31, 1601-1604; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Maeda, N.; Imanishi, T.; Tanaka, T. Heterocycles 1991, 32, 2471-2478; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Nakamoto, Y.; Sakae, M.; Katsurada, M.; Imanishi, T.; Tanaka, T. J. Chem. Soc., Chem. Commun. 1992, 1379-1381; Tanaka, T; Watanabe, M.; Nakamoto, Y.; Okuno, K.; Maekawa, K.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 2301-2302; Tanaka, T.; Nakamoto, Y.; Maekawa, K.; Watanabe, M.; Nishihara, C.; Iwata, C. Heterocycles 1996, 42, 265-272.
8. Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Heterocycles 1988, 27, 323-326; Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M.; Imanishi, T. Synthesis 1988, 261-262; Iwata, C.; Fujimoto, M.; Okamoto, S.; Nishihara, C.; Sakae, M.; Katsurada, M.; Watanabe, M.; Kawakami, T.; Tanaka, T.; Imanishi, T. Heterocycles 1990, 31, 1601-1604; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Maeda, N.; Imanishi, T.; Tanaka, T. Heterocycles 1991, 32, 2471-2478; Iwata, C.; Fujimoto, M.; Watanabe, M.; Kawakami, T.; Nakamoto, Y.; Sakae, M.; Katsurada, M.; Imanishi, T.; Tanaka, T. J. Chem. Soc., Chem. Commun. 1992, 1379-1381; Tanaka, T; Watanabe, M.; Nakamoto, Y.; Okuno, K.; Maekawa, K.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 2301-2302; Tanaka, T.; Nakamoto, Y.; Maekawa, K.; Watanabe, M.; Nishihara, C.; Iwata, C. Heterocycles 1996, 42, 265-272.
9. Iwata, C.; Kawakami, T.; Fujimoto, M.; Nakamoto, Y.; Tanaka, T. Heterocycles 1993, 36, 55-62.
10. For a review of sulfur ylides, see Trost, B. M.; Melvin Jr., L. S. "Sulfur Ylides", Academic Press, New York, 1975.
11. Yields of sulfoxides (4) and sulfones (5): 4a (47 %), 5a (35 %); 4b (61 %), 5b (30 %); 4c (60 %), 5c (27 %); 4d (56 %), 5d (36 %).
12. For reviews, see Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760; Marino, J. P. Pure Appl. Chem. 1993, 65, 667-674; De Lucchi, O.; Miotti, U.; Modena, G. "Organic Reactions," ed. by Paquette, L. A. John Wiley & Sons, Inc., New York, 1991, Vol. 40, pp. 157-405; Kennedy, M.; McKervey, M. A. "Comprehensive Organic Synthesis", ed. by Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991, Vol. 7, pp. 193-206.
13. For reviews, see Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760; Marino, J. P. Pure Appl. Chem. 1993, 65, 667-674; De Lucchi, O.; Miotti, U.; Modena, G. "Organic Reactions," ed. by Paquette, L. A. John Wiley & Sons, Inc., New York, 1991, Vol. 40, pp. 157-405; Kennedy, M.; McKervey, M. A. "Comprehensive Organic Synthesis", ed. by Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991, Vol. 7, pp. 193-206.
14. For reviews, see Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760; Marino, J. P. Pure Appl. Chem. 1993, 65, 667-674; De Lucchi, O.; Miotti, U.; Modena, G. "Organic Reactions," ed. by Paquette, L. A. John Wiley & Sons, Inc., New York, 1991, Vol. 40, pp. 157-405; Kennedy, M.; McKervey, M. A. "Comprehensive Organic Synthesis", ed. by Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991, Vol. 7, pp. 193-206.
15. For reviews, see Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760; Marino, J. P. Pure Appl. Chem. 1993, 65, 667-674; De Lucchi, O.; Miotti, U.; Modena, G. "Organic Reactions," ed. by Paquette, L. A. John Wiley & Sons, Inc., New York, 1991, Vol. 40, pp. 157-405; Kennedy, M.; McKervey, M. A. "Comprehensive Organic Synthesis", ed. by Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991, Vol. 7, pp. 193-206.
16. Cf. Tokitoh, N.; Igarashi, Y.; Ando, W. Tetrahedron Lett. 1987, 28, 5903-5906; McIntosh, J. M.; Leavitt, R. K. Can. J. Chem. 1985, 63, 3313-3316.
17. Cf. Tokitoh, N.; Igarashi, Y.; Ando, W. Tetrahedron Lett. 1987, 28, 5903-5906; McIntosh, J. M.; Leavitt, R. K. Can. J. Chem. 1985, 63, 3313-3316.
18. 3, 200 MHz) δ: 2.77 (3H, d), 2.94 (3H, s), 3.31 (2H, t), 3.82 (2H, t), 4.49 (2H, s), 4.60 (1H, br), 7.18-7.42 (5H, m).
19. WF = 0.229.
20. a) Andreasch, R. Monatsh. Chem. 1883, 4, 131-148;
21. b) Wolfbauer, H. Monatsh. Chem. 1904, 25, 682-686;
22. c) Hoogenboom, B. E.; Abbott, R.; Locatell Jr., L.; Hinman, R. L. J. Org. Chem. 1959, 24, 1983-1986;
23. d) Hasegawa, K.; Hirooka, S. Bull. Chem. Soc. Jpn. 1972, 45, 1893-1896.
24. For a review of thiadiazine derivatives, see e) Lawson, A.; Tinkler, R. B. Chem. Rev. 1970, 70, 593-618; f) Busby, R. E. Advances in Heterocyclic Chemistry; Katrizky, A. R., Ed.; Academic Press; New York; 1990; Vol. 50; pp. 255-320.
25. For a review of thiadiazine derivatives, see e) Lawson, A.; Tinkler, R. B. Chem. Rev. 1970, 70, 593-618; f) Busby, R. E. Advances in Heterocyclic Chemistry; Katrizky, A. R., Ed.; Academic Press; New York; 1990; Vol. 50; pp. 255-320.
26. Novello, F. C.; Sprague, J. M. J. Am. chem. Soc. 1957, 79, 2028-2029; Rubin, A. A.; Roth, F. E.; Winbury, M. M.; Topliss, J. G.; Sherlock, M. H.; Sperber, N.; Black, J. Science, 1961, 133, 2067; Landquist, J. K. Comprehensive Organic Chemistry; Barton, D.; Ollis, W. D. Ed.; Pergamon Press; Oxford; 1979; Vol. 4; p. 1114-1121.
27. Novello, F. C.; Sprague, J. M. J. Am. chem. Soc. 1957, 79, 2028-2029; Rubin, A. A.; Roth, F. E.; Winbury, M. M.; Topliss, J. G.; Sherlock, M. H.; Sperber, N.; Black, J. Science, 1961, 133, 2067; Landquist, J. K. Comprehensive Organic Chemistry; Barton, D.; Ollis, W. D. Ed.; Pergamon Press; Oxford; 1979; Vol. 4; p. 1114-1121.
28. Novello, F. C.; Sprague, J. M. J. Am. chem. Soc. 1957, 79, 2028-2029; Rubin, A. A.; Roth, F. E.; Winbury, M. M.; Topliss, J. G.; Sherlock, M. H.; Sperber, N.; Black, J. Science, 1961, 133, 2067; Landquist, J. K. Comprehensive Organic Chemistry; Barton, D.; Ollis, W. D. Ed.; Pergamon Press; Oxford; 1979; Vol. 4; p. 1114-1121.
29. We later found that N-Me-sulfoxide (11) was easily oxidized to a sulfone by m-CPBA in good yield.
30. S-Alkylation has been noted previously in the alkylation reaction of sulfinate anion with a soft alkylating agent such as MeI to give a sulfone instead of an ester. See, Meek, J. S.; Fowler, J. S. J. Org. Chem. 1968, 33, 3422-3424.