A facile construction of 4-hydroxymethylbenzisothiazolone-1,1-dioxide

Tetrahedron Letters

Volumn 39, Issue 12, 1998, Pages 1483-1486

  Yeung, Kap Sun ^a   Meanwell, Nicholas A ^a   Li, Yi ^a   Gao, Qi ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURFURYL ALCOHOL;

AROMATIZATION; ARTICLE; HYDROGEN BOND; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032546235     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00011-2     Document Type: Article

References (29)

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3. (c) Sunkel, C. E.; de Casa-Juana, M. F.; Cillero, F. J.; Priego, J. G.; Ortega, M. P. J. Med. Chem. 1988, 31, 1886.
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6. (f) Silver, P. J.; Gordon, R. J.; Pagani, E. D.; Johnson, J. A.; Maycock, A. L.; Dunlap, R. P.; Ferguson, E. W.; Franke, C. A.; Drozd, M. L.; Robinson , D. T.; Eickhoff, W. M.; Baizman, E. R.; Subramanyam, C.; Desai, R. C.; Hlasta, D. J.; Newton, J. F. Drug Development Res. 1995, 34, 306 and reference cited therein.
7. (2) (a) Dunlap, R. P.; Boaz, N. W.; Mura, A. J.; Kumar, V.; Subramanyam, C.; Desai, R. C.; Hlasta, D. J.; Saindane, M. T.; Bell, M. R.; Court, J. J.; Farrell, R. P. Patent, US 5,512,589 (Apr: 30, 1996).
8. (b) For nitro derivatives see Saari, W. S.; Schwering, J. E. J. Heterocyclic Chem. 1986, 23, 1253.
9. (3) Related studies: (a) Weiler, E. D.; Brennan, J. J. J. Heterocyclic Chem. 1978, 15, 1299.
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12. (d) Burri, K. F. Helv. Chim. Acta 1990, 73, 69.
13. (e) For related system using α,β-unsaturated hydrazones as dienes see
14. (i) Waldner, A. Helv. Chim. Acta 1989, 72, 1435.
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16. (4) 2-(terf-Butyl)-isothiazolone-1,1-dioxide 2 was prepared from 3,3א-dithiodipropanoicacid according to literature procedures: (a) Lewis, S. N.; Millar, G. A.; Hausman, M.; Szamborski, E. C. J. Heterocyclic Chem. 1971, 8, 571.
17. (b) Lewis, S. N.; Millar, G. A.; Hausman, M.; Szamborski, E. C. J. Heterocyclic Chem. 1971, 8, 591.
18. (c) Burri, K. F. Helv. Chim. Acta 1989, 72, 1416.
19. 1H NMR analysis on the crude reaction mixture indicated a 1.3:1 ratio of exo/endo products. Sometimes, a 2:1 ratio could be obtained. The reaction could not be carried out at high temperature due to the thermal instability of furfuryl alcohol.
20. (6) For convenience, the numbering of benzisothiazolone-1,1-dioxide is used.
21. tBu).
22. (8) Ref. 3(d) and Burri, K. F. Chimia 1992, 46, 335.
23. b (a) Fair, C. K. (1990). MolEN. An Interactive Intelligent System for Crystal Structure Analysis. Enraf-Nonius, Delft, The Netherlands.
24. (b) Atomic coordinates, thermal parameters, bond lengths and angles have been deposited with the Cambridge Crystallographic Data Center and can be obtained upon request.
25. (10) Calculations were performed using Gaussian 94, Revision A.1, Gaussian, Inc., Pittsburgh PA, 1995. For a detailed discussion of this method, see: (a) Mller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
26. (b) Hehre, W.J.; Radom, L.; Schleyer, P.V. R.; Pople, J.A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
27. (11) Houk, K. N.; Gonzalez, J.; Li, Y. Acct. Chem. Res. 1995, 28, 81.
28. (12) The reaction yield was reduced to 33% in the absence of TMSCl.
29. (13) Presumably, dehydration of the endo isomer 4 under basic conditions involves unfavorable syn elimination, whereas favorable anti elimination takes place for the exo isomer 3.