Synthesis and stereochemistry of stereoisomeric 1,2,3-oxathiazino[4,3-a]isoquinolines

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 2, 2000, Pages 287-293

  Sohár, Pál ^a   Forró, Enikö ^a   Lázár, László ^a   Bernáth, Gábor ^a   Sillanpää, Reijo ^a   Fülöp, Ferenc ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

HOMOCALYCOTOMINE; STEREOISOMERIC OXATHIAZINOISOQUINOLINES; SULFURYL CHLORIDE; THIONYL CHLORIDE;

ORGANIC COMPOUNDS;

EID: 0034143067     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907236e     Document Type: Article

References (40)

1. J. W. Guiles and A. I. Meyers, J. Org. Chem., 1991, 56, 6873.
2. M. Sugiura, N. Takao, H. Fujiwara and Y. Sasaki, Chem. Pharm. Bull., 1978, 26, 2555.
3. M. Rubiralta, A. Diez and J. Bosch, Heterocycles, 1988, 27, 1653.
4. P. Scheider and P. Nemes, Heterocycles, 1995, 41, 2189.
5. J. Kóbor, P. Sohár and F. Fülöp, Tetrahedron, 1994, 50, 4873.
6. G. Bernáth, F. Fülöp et al., Hung. Pat. 209393, Chem. Abstr., 1993, 119, 225960.
7. F. Fülöp, G. Bernáth, M. S. El-Gharib, J. Kóbor, P. Sohár, I. Pelczer, G. Argay and A. Kálmán, Chem. Ber., 1990, 123, 803.
8. P. Sohár, L. Lázár, F. Fülöp, G. Bernáth and J. Kóbor, Tetrahedron, 1992, 48, 4937.
9. B. E. Maryanoff, D. F. McComsey, R. R. Inners, M. S. Mutter, G. P. Wooden, S. L. Mayo and R. A. Olofson, J. Am. Chem. Soc., 1989, 111, 2487.
10. T. Viljanen, K. Pihlaja and F. Fülöp, Acta Chem. Scand., 1996, 50, 1036.
11. Z. Zubovics, L. Toldy, A. Varró, G. Rablóczky, P. Dvortsák, G. Jerkovich and É. Tomori, Eur. J. Med. Chem., 1986, 21, 370.
12. R. J. Goodridge, T. W. Hambley and D. D. Ridley, Aust. J. Chem., 1986, 39, 591.
13. V. K. Aggarwal, J. M. Worrall, H. Adams, R. Alexander and B. F. Taylor, J. Chem. Soc., Perkin Trans. 1, 1997, 21.
14. G. Lowe and M. A. Reed, Tetrahedron: Asymmetry, 1990, 1, 885.
15. D. Alker, K. J. Doyle, L. M. Harwood and A. McGregor, Tetrahedron: Asymmetry, 1990, 1, 877.
16. J. E. Baldwin, A. C. Spivey and C. J. Schofield, Tetrahedron: Asymmetry, 1990, 1, 881.
17. H. S. H. Gautun and P. H. J. Carlsen, Tetrahedron: Asymmetry, 1995, 6, 1667.
18. The compounds studied were racemates. In Scheme 1 and the Figures, C-1 (for 3, 4 and 7, 8) or C-11b (for 9-23) is drawn R*.
19. J. Kóbor, F. Fülöp, G. Bernáth and P. Sohár, Tetrahedron, 1986, 43, 1887.
20. S. E. Schaus, J. F. Larrow and E. N. Jacobsen, J. Org. Chem., 1997, 62, 4197.
21. M. J. Karplus, Chem. Phys., 1959, 30, 11
22. M. J. Karplus, Chem. Phys., 1960, 33, 1842.
23. P. Sohár, Nuclear Magnetic Resonance Spectroscopy, CRC Press, Boca Raton, FL, 1983, (a) 2, 154-155
24. P. Sohár, Nuclear Magnetic Resonance Spectroscopy, (b) 1, 34
25. P. Sohár, Nuclear Magnetic Resonance Spectroscopy, (c) 1, 196-197
26. P. Sohár, Nuclear Magnetic Resonance Spectroscopy, (d) 2, 152-154;
27. P. Sohár, Nuclear Magnetic Resonance Spectroscopy, (e) 1, 35-38
28. P. Sohár, Nuclear Magnetic Resonance Spectroscopy, (f) 2, 166
29. P. Sohár, Nuclear Magnetic Resonance Spectroscopy, (g) 2, 27.
30. D. M. Grant and B. V. Cheney, J. Am. Chem. Soc., 1967, 89, 5315.
31. J. K. M. Sanders and J. D. Mersch, Prog. Nucl. Magn. Reson., 1982, 15, 353, and references cited therein.
32. J. Mason, J. Chem. Soc., 1971, 1038.
33. R. R. Ernst, G. Bodenhausen and A. Wokaun, Principles of Nuclear Magnetic Resonance in One and Two Dimensions, Clarendon Press, Oxford, UK, 1987, (a) pp. 400-426
34. R. R. Ernst, G. Bodenhausen and A. Wokaun, Principles of Nuclear Magnetic Resonance in One and Two Dimensions, (b) pp. 471-479.
35. D. T. Pegg, D. M. Doddrell and M. R. Bendall, J. Chem. Phys., 1982, 77, 2745.
36. M. R. Bendall, D. M. Doddrell, D. T. Pegg and W. E. Hull, High Resolution Multipulse NMR Spectrum Editing and DEPT, Bruker, Karlsruhe, 1982.
37. J. Kóbor, F. Fülöp and G. Bernáth, Heterocycles, 1986, 24, 2227.
38. International Tables for X-Ray Crystallography, Kynoch Press, Birmingham, UK, 1974, Vol. IV.
39. teXsan for Windows: Single Crystal Structure Analysis Software, Version 1.01. Molecular Structure Corporation, 3200 Research Forest Drive, The Woodlands, TX 77381, 1997.
40. C. K. Johnson, ORTEP-II, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN 1976.