A Pummerer-Type Novel Ring Fission of 2-Methylsulfinyl-5,6-dihydro-4H-1,3,4-thiadiazine Derivatives: A Homologation of Aldehydes and Ketones

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 4, 1996, Pages 1043-1054

  Shimada, Kazuaki ^a   Otaki, Akihiro ^a   Yanakawa, Masaki ^a   Mabuchi, Shosuke ^a   Yamakado, Naoya ^a   Shimoguchi, Takeshi ^a   Inoue, Kazuya ^a   Kagawa, Takashi ^a   Shoji, Kazutoshi ^a   Takikawa, Yuji ^a  

^a IWATE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041435222     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.1043     Document Type: Article

References (34)

1. M. Busch and M. Starke, J. Prakt. Chem., 93, 59 (1916).
2. a) R. Andreasch, Monatsh. Chem., 27, 1211 (1906);
3. b) S. M. Losanitch, J. Chem. Soc., 119, 763 (1921);
4. c) P. K. Bose, Q. J. Indian Chem. Soc., 3, 197 (1926);
5. d) J. Sandström, Ark. Kemi., 7, 249 (1952);
6. e) J. Sandström, Ark. Kemi., 4, 297 (1952);
7. f) R. A. Mathes, J. Org. Chem., 17, 877 (1952);
8. g) R. Hull, J. Chem. Soc., 1952, 2959;
9. h) H. Beyer, W. Lassig, and E. Bulka, Chem. Ber., 87, 1385 (1954);
10. i) T. Sato and M. Ohta, Yakugaku Zasshi, 77, 771 (1957);
11. j) J. Sandström, Acta Chem. Scand., 16, 2395 (1962);
12. k) D. L. Trepanier, W. Reifschneider, W. Shumaker, and D. S. Tharpe, J. Org. Chem., 30, 2228 (1965);
13. l) D. L. Trepanier and P. E. Krieger, J. Heterocycl. Chem., 4, 254 (1967);
14. m) Y. Usui and T. Yamano, Yakugaku Zasshi, 89, 689 (1969);
15. n) Y. Usui and T. Yamano, Yakugaku Zasshi, 89, 699 (1969);
16. o) J. Beger, C. Thilemann, and P. D. Thong, J. Prakt. Chem., 321, 959 (1979);
17. p) S. Kubota, Y. Ueda, K. Fujikane, K. Toyooka, and M. Shibuya, J. Org. Chem., 45, 1473 (1980);
18. q) S. H. Askari, S. F. Moss, and D. R. Taylor, J. Chem. Soc., Perkin Trans. 1, 1981, 360;
19. r) S. Kubota, K. Toyooka, J. Ikeda, N. Yamamoto, and M. Shibuya, J. Chem. Soc., Perkin Trans. 1, 1983, 967;
20. s) Y. Nakayama and Y. Sanemitsu, J. Org. Chem., 49, 1703 (1984);
21. t) Y. Nakayama and Y. Sanemitsu, Synthesis, 1984, 771;
22. u) S. V. Usol'tseva, G. P. Andronnikova, S. L. Nikolaeva, A. T. Lebedev, and V. A. Shevyrin, Khim. Gelerotsikl. Soedin., 1991, 554;
23. v) W. Hanefeld and M. Schlitzer, Arch. Pharm., 326, 249 (1993).
24. D. M. Evans, D. R. Taylor, and M. Myers, J. Chem. Soc., Chem. Commun., 1984, 1444.
25. F. Babudri, S. Florio, A. Reho, and G. Trapani, J. Chem. Soc., Perkin Trans. 1, 1984, 1949, and the references cited therein.
26. K. Shimada, A. Otaki, M. Yanakawa, S. Mabuchi, N. Yamakado, T. Shimoguchi, K. Inoue, T. Kagawa, K. Shoji, and Y. Takikawa, Chem. Lett., 1995, 925.
27. O. De Lucchi, U. Miotti, and G. Modena, "Organic Reactions," ed by L. A. Paquette, (1991), Vol. 40, p. 157, and the references cited therein.
28. For example, the J value of H-5 and H-6 of trans-6a was 9 Hz. On the other hand, that of cis-6a was 3 Hz.
29. R. R. Schmidt, Angew. Chem., 87, 603 (1975), and the references cited therein.
30. W. D. Pfeiffer, E. Bulka, and R. Miethchen, Z. Chem., 27, 296 (1987), and the references cited therein.
31. E. Wertheim, J. Am. Chem. Soc., 48, 826 (1926).
32. S. Manogaran and D. N. Sathyanarayana, Bull. Chem. Soc. Jpn., 55, 2628 (1982), and the references cited therein.
33. K. V. Awers, J. Prakt. Chem., 105, 361 (1923).
34. K. Sasaki, Bull. Chem. Soc. Jpn., 40, 2968 (1967).