Synthesis and structural characteristics of novel 5H-thiazolo[2,3-d][1,5]benzothiazepine derivatives

Abstract

The 5H-thiazolo[2,3-d][1,5]benzothiazepines 13–16 have been synthesized by condensation of the 1,5-benzothiazepine-2-thiones 5–8 and α-bromoacetaldehyde diethyl acetal followed by treatment with alkali. The structure and stereochemistry of the adducts obtained has been established on the basis of spectroscopic data. For compounds 15 and 16 the presence in solution of two conformers has been postulated. An X-ray crystallographic structural study of thiazolobenzothiazepine 15 reveals that only one conformer is present in the solid state, stabilized by the presence of a short S · · ·   O contact (2.59 Å).

References

1. A. Chimirri, R. Gitto, S. Grasso, A. M. Monforte and M. Zappalà, Adv. Heterocycl. Chem., 1995, 63, 61.
2. (a) G. Capozzi, A. Chimirri, S. Grasso, G. Romeo and G. Zappia, Heterocycles, 1985, 23, 2051; (b) M. Zappalà, A. Chimirri, S. Grasso, G. Romeo and A. M. Monforte, Il Farmaco, Ed. Sc., 1989, 44, 185; (c) A. Chimirri, S. Grasso, A. M. Monforte, G. Romeo and M. Zappalà, Heterocycles, 1993, 36, 691.
3. A. Chimirri, R. Gitto, S. Grasso, P. Monforte and M. Zappalà, Heterocycles, 1994, 38, 2289.
4. W. Ried and G. Sell, Chem. Ber., 1980, 113, 2314.
5. (a) J. Krapcho, E. R. Spitzmiller and C. F. Turk, J. Med. Chem., 1963, 6, 544; (b) B. Letois, J. C. Lancelot, C. Saturnino, M. Robba and P. De Caprariis, J. Heterocycl. Chem., 1992, 29, 1769.
6. V. Ambrogi, G. Grandolini, L. Perioli, L. Giusti, A. Lucacchini and C. Martini, Il Farmaco, 1993, 48, 665.
7. G. Kaupp and D. Matthies, Chem. Ber., 1987, 120, 1741.
8. D. Cremer and J. A. Pople, J. Am. Chem. Soc., 1975, 97, 1354.
9. M. Nardelli, Acta Crystllogr., Sect. C, 1983, 39, 1141.
10. (a) L. Jiang, S. Liu, G. Li, H. Wu and S. Jin, Chem. Res. Chin. Univ., 1992, 8, 247; (b) L. Jiang, S. Liu, G. Li, H. Wu and S. Jin, Jiegou Huaxue (J. Struct. Chem.), 1992, 11, 297.
11. F. H. Allen, J. E. Davies, J. J. Galloy, O. Johnson, O. Kennard, C. F. Macrae, E. M. Mitchell, G. F. Mitchell, J. M. Smith and D. G. Watson, J. Chem. Info. Comp. Sci., 1991, 31, 187.
12. D. P. Hansell, K. J. Robinson, J. D. Wallis and D. C. Povey, Acta Crystallogr., Sect. C, 1996, 52, 136.
13. The calculations were carried out, on the X-ray refined model, using AMPAC 5.0 program (© 1994 Semichem, 7128 Summit, Shawnee, KS 66216), in which AM1 option is included: cf. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.
14. (a) J. G. Angyan, R. A. Poirier, A. Kucsman and I. G. Csizmadia, J. Am. Chem. Soc., 1987, 109, 2237; (b) R. F. Hudson, J. D. Wallis and P. Hansell, Heterocycles, 1994, 37, 1933; (c) A. N. Dixit, K. V. Reddy, A. R. A. S. Deshmukh, S. Rajappa, B. Ganguly and J. Chandrasekhar, Tetrahedron, 1995, 51, 1437; (d) H. Jacobsen, H. K. Kraatz, T. Ziegler and P. M. Boorman, J. Am. Chem. Soc., 1992, 114, 7851.
15. (a) D. H. R. Barton, M. B. Hall, Z. Lin, S. I. Parekh and J. Reibenspies, J. Am. Chem. Soc., 1993, 115, 5056; (b) F. T. Burling and B. M. Goldstein, J. Am. Chem. Soc., 1992, 114, 2313; (c) T. Chivers, I. Krouse, M. Parvez, I. Vargas-Baca, T. Ziegler and P. Zoricak, Inorg. Chem., 1996, 35, 5836.
16. A. Altomare, O. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori and M. Camalli, J. Appl. Cryst., 1994, 27, 435.
17. G. M. Sheldrick, SHELXTL Plus, Release 4.21, Siemens Analytical X-Ray Instruments Inc., Madison, Wisconsin, USA, 1990.
18. G. M. Sheldrick, SHELXL-93, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1993.
19. International Tables for Crystallography, vol. C, ed. A. J. C. Wilson, Kluwer Academic Publishers, Boston, 1992, Tables 4.2.6.8 and 6.1.1.4.