Ring–ring interconversion: the rearrangement of 6-(4-chlorophenyl)-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazole into 8-(4-chlorophenyl)-8-hydroxy-5-methyl-8H-[1,4]thiazino[3,4-c][1,2,4]oxadiazol-3-one. Elucidation of the reaction product through spectroscopic and X-ray crystal structure analysis

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Aldo Andreani, Roberta Billi, Barbara Cosimelli, Angelo Mugnoli, Mirella Rambaldi and Domenico Spinelli


Abstract

The reactivity of 6-(4-chlorophenyl)-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazole (a member of a class of mutagenic compounds) with hydrochloric acid in ethanol has been investigated and the nature of the reaction product unambiguously established on the basis of infrared, NMR and mass spectra and a crystal structure determination.


References

  1. (a) P. Hrelia, F. Vigagni, F. Maffei, C. Fimognari, L. Lamartina, D. Spinelli, P. Juric, M. C. Guerra and G. Cantelli Forti, Mutagenesis, 1995, 10, 171 Search PubMed; P. Hrelia, F. Vigagni, M. Morotti, G. Cantelli Forti, C. I. Barbieri, D. Spinelli and I. Lamartina, Chem.-Biol. Interactions, 1993, 86, 229 Search PubMed; (b) A. Andreani, M. Rambaldi, F. Andreani, P. Hrelia and G. Cantelli Forti, Arch. Pharm. Chemi. Sci. Ed., 1987, 15, 41 Search PubMed.
  2. M. Ruccia, N. Vivona and D. Spinelli, Adv. Heterocycl. Chem., 1981, 29, 141 CAS; V. Frenna, G. Macaluso, N. Vivona, D. Spinelli, G. Consiglio and E. Mezzina, Tetrahedron, 1994, 50, 7315 CrossRef CAS.
  3. D. Spinelli, A. Mugnoli, A. Andreani, M. Rambaldi and S. Frascari, J. Chem. Soc., Chem. Commun., 1992, 1394 RSC.
  4. Drug Metabolism in Man, ed. J. W. Gorrod and A. H. Beckett, Taylor and Francis, London, 1978 Search PubMed.
  5. P. Hrelia, L. Murelli, M. Paolini, E. Sapigni and G. Cantelli Forti, Mutagenesis, 1987, 2, 425 Search PubMed and references cited therein.
  6. A. C. T. North, D. C. Phillips and F. S. Mathews, Acta Crystallogr., Sect. A, 1968, 24, 351 CrossRef.
  7. E. J. Gabe, Y. Le Page, J.-P. Charland, F. L. Lee and P. S. White, J. Appl. Crystallogr., 1989, 22, 384 CrossRef.
  8. G. M. Sheldrick, SHELXL93, Program for Refinement of Crystal Structures, University of Göttingen, 1993.
  9. M. Nardelli, PARST, Comput. Chem., 1983, 7, 95 CrossRef CAS.
  10. D. Spinelli, Thesis, University of Bari, 1955; S. Cusmano and M. Ruccia, Gazz. Chim. Ital., 1955, 85, 1686 Search PubMed; S. Cusmano and M. Ruccia, Gazz. Chim. Ital., 1958, 88, 463 CAS.
  11. B. Cavalleri, P. Bellani and G. Lancini, J. Heterocycl. Chem., 1973, 10, 357 CAS.
  12. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1 RSC.
  13. F. H. Allen and O. Kennard, Chemical Design Automation News, 1993, 8, 1, 31 Search PubMed.
  14. M. Nardelli, Acta Crystallogr., Sect. C, 1983, 39, 1141 CrossRef; W. L. Duax, C. M. Weeks and D. C. Rohrer, Top. Stereochem., 1976, 9, 271 Search PubMed.
  15. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902 CrossRef.
  16. J. J. P. Stewart, MOPAC, QCPE Bull., 1983, 3, 43 Search PubMed.
  17. The low resonance energy of the –CO–S– group means it can act as an acylating agent via SNAc reactions. Several aspects of this reactivity are well supported in chemical (see M. J. Janssen, The Chemistry of Carboxylic Acids and Esters, ed. S. Patai, Interscience, New York, 1969, p. 724 and following) and biological (see the role of acetyl coenzyme A in biological acylation) systems Search PubMed.
  18. L. Fournier, A. Natat, G. Lamaty and J. P. Roque, Recl. Trav. Chim. Pays-Bas, 1972, 91, 1015 CAS; M. E. Peach, in The Chemistry of the Thiol Group, ed. S. Patai, Wiley, New York, 1974, p. 765 and following Search PubMed; T. H. Lowry and K. Schneller Richardson, Mechanism and Theory in Organic Chemistry, Harper and Row, 3rd edn., 1987, pp. 701–702 and references cited therein Search PubMed.
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