Oxidation of 2-phenylhydrazono-γ-butyrolactone: A novel ring expansion rearrangement leading to tetrahydro-1,3-oxazine-2,4-dione derivatives

Chemical Communications

Volumn , Issue 6, 1997, Pages 571-572

  Barton, Derek H R ^a   Liu, Wansheng ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542394896     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a607830c     Document Type: Article

References (26)

1. Z. Eckstein and T. Urbanski, Adv. Heterocycl. Chem., 1963, 2, 311; Z. Eckstein and T. Urbanski, Adv. Heterocycl. Chem., 1978, 23, 1; T. Kato, N. Katagiri and Y. Yamamoto, Heterocycles, 1980, 14, 1333.
2. Z. Eckstein and T. Urbanski, Adv. Heterocycl. Chem., 1963, 2, 311; Z. Eckstein and T. Urbanski, Adv. Heterocycl. Chem., 1978, 23, 1; T. Kato, N. Katagiri and Y. Yamamoto, Heterocycles, 1980, 14, 1333.
3. Z. Eckstein and T. Urbanski, Adv. Heterocycl. Chem., 1963, 2, 311; Z. Eckstein and T. Urbanski, Adv. Heterocycl. Chem., 1978, 23, 1; T. Kato, N. Katagiri and Y. Yamamoto, Heterocycles, 1980, 14, 1333.
4. A. I. Meyers, Heterocycles in Organic Synthesis, Wiley, New York, 1974, pp. 160-266; R. R. Schmidt, Synthesis, 1972, 333.
5. A. I. Meyers, Heterocycles in Organic Synthesis, Wiley, New York, 1974, pp. 160-266; R. R. Schmidt, Synthesis, 1972, 333.
6. T. Haneishi, T. Okazaki, T. Hata, C. Tamuta, M. Namura, A. Naito, I. Seki and M. Arai, J. Antibiot., 1971, 24, 797; K. Sasaki, Y. Kusakabe and S. Esumi, J. Antibiot., 1972, 25, 151; Y. Kusakabe, J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose and S. Shirato, J. Antibiot., 1972, 25, 44; D. B. Silvano and W. Manfred, J. Org. Chem., 1972, 42, 109.
7. T. Haneishi, T. Okazaki, T. Hata, C. Tamuta, M. Namura, A. Naito, I. Seki and M. Arai, J. Antibiot., 1971, 24, 797; K. Sasaki, Y. Kusakabe and S. Esumi, J. Antibiot., 1972, 25, 151; Y. Kusakabe, J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose and S. Shirato, J. Antibiot., 1972, 25, 44; D. B. Silvano and W. Manfred, J. Org. Chem., 1972, 42, 109.
8. T. Haneishi, T. Okazaki, T. Hata, C. Tamuta, M. Namura, A. Naito, I. Seki and M. Arai, J. Antibiot., 1971, 24, 797; K. Sasaki, Y. Kusakabe and S. Esumi, J. Antibiot., 1972, 25, 151; Y. Kusakabe, J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose and S. Shirato, J. Antibiot., 1972, 25, 44; D. B. Silvano and W. Manfred, J. Org. Chem., 1972, 42, 109.
9. T. Haneishi, T. Okazaki, T. Hata, C. Tamuta, M. Namura, A. Naito, I. Seki and M. Arai, J. Antibiot., 1971, 24, 797; K. Sasaki, Y. Kusakabe and S. Esumi, J. Antibiot., 1972, 25, 151; Y. Kusakabe, J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose and S. Shirato, J. Antibiot., 1972, 25, 44; D. B. Silvano and W. Manfred, J. Org. Chem., 1972, 42, 109.
10. M. S. von Wittenau and H. Els, J. Am. Chem. Soc., 1961, 83, 4678.
11. M. Sainsbury, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon, New York, 1984, vol. 3, pp. 995-1038.
12. D. H. R. Barton, J. C. Jaszberenyi, W. Liu and T. Shinada, Tetrahedron, 1996, 52, 2717.
13. R. H. Harradence and F. Lions, J. Proc. Royal Soc. N. S. Wales, 1938, 72, 221.
14. D. H. R. Barton, J. Cs. Jaszberenyi, W. Liu and T. Shinada, Tetrahedron, 1996, 52, 14 673.
15. L. Kletz and A. Lapworth, J. Chem. Soc., 1915, 107, 1254.
16. P. C. Huang and E. M. Kosower, J. Am. Chem. Soc., 1968, 90, 2354.
17. E. M. Kosower, Acc. Chem. Res., 1971, 4, 193.
18. P. C. Huang and E. M. Kosower, J. Am. Chem. Soc., 1968, 90, 2367.
19. H. Schinz and M. Hinder, Helv. Chim. Acta, 1947, 30, 1349; C. G. Wermuth, Bull. Soc. Chim. Fr., 1966, 1435; H. H. Wasserman and J. L. Ives, J. Org. Chem., 1978, 43, 3238; I. Tapia, V. Alcazar, J. R. Moran, C. Caballero and M. Grande, Chem. Lett., 1990, 697.
20. H. Schinz and M. Hinder, Helv. Chim. Acta, 1947, 30, 1349; C. G. Wermuth, Bull. Soc. Chim. Fr., 1966, 1435; H. H. Wasserman and J. L. Ives, J. Org. Chem., 1978, 43, 3238; I. Tapia, V. Alcazar, J. R. Moran, C. Caballero and M. Grande, Chem. Lett., 1990, 697.
21. H. Schinz and M. Hinder, Helv. Chim. Acta, 1947, 30, 1349; C. G. Wermuth, Bull. Soc. Chim. Fr., 1966, 1435; H. H. Wasserman and J. L. Ives, J. Org. Chem., 1978, 43, 3238; I. Tapia, V. Alcazar, J. R. Moran, C. Caballero and M. Grande, Chem. Lett., 1990, 697.
22. H. Schinz and M. Hinder, Helv. Chim. Acta, 1947, 30, 1349; C. G. Wermuth, Bull. Soc. Chim. Fr., 1966, 1435; H. H. Wasserman and J. L. Ives, J. Org. Chem., 1978, 43, 3238; I. Tapia, V. Alcazar, J. R. Moran, C. Caballero and M. Grande, Chem. Lett., 1990, 697.
23. H. Meerwein, Org. Synth., 1973, Coll. Vol. 5, 1080.
24. S. Ozaki and T. Kato, J. Polym. Sci., C, 1968, 695.
25. T. L. Gresham, J. E. Jansen, F. W. Shaver, J. T. Gregory and W. L. Beears, J. Am. Chem. Soc., 1948, 70, 1004.
26. H. Yamamoto, J. Org. Chem., 1967, 32, 3693.