An Efficient Novel Synthesis of Hydroxy- and Alkoxysultams Using MMPP as Oxidant of Isothiazolium Salts

Synthesis

Volumn , Issue 14, 2003, Pages 2265-2268

  Taubert, Kathleen ^a   Siegemund, Anja ^a   Eilfeld, Alexander ^a   Baumann, Sven ^a   Sieler, Joachim ^a   Schulze, Bärbel ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

Hydroperoxides; Magnesium monoperoxyphthalate (MMPP); Oxidation; Sultams

Indexed keywords

ETHANOL; MAGNESIUM PRINTING PLATES; OXIDATION; ULTRASONICS;

ULTRASOUND BATH;

SYNTHESIS (CHEMICAL);

2,3 DIHYDRO 3 METHOXY 4,5 DIMETHYL 2 (4 METHYLPHENYL)ISOTHIAZOLE 1,1 DIOXIDE; ALCOHOL; ALKOXYSULTAM DERIVATIVE; HYDROXYSULTAM DERIVATIVE; ISOTHIAZOLE DERIVATIVE; OXIDIZING AGENT; PEROXYPHTHALATE MAGNESIUM; PHTHALIC ACID DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ANALYTIC METHOD; ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION; ULTRASOUND;

EID: 0142025306     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42087     Document Type: Article

References (26)

1. De, A. Prog. Med. Chem. 1981, 18, 117.
2. Schulze, B.; Illgen, K. J. Prakt. Chem. 1997, 339, 1.
3. Taubert, K.; Kraus, S.; Schulze, B. Sulfur Reports 2002, 23, 79.
4. Siegemund, A.; Taubert, K.; Schulze, B. Sulfur Reports 2002, 23, 279.
5. Davis, M. Adv. Heterocycl. Chem. 1985, 38, 105.
6. Burri, K. F. Helv. Chim. Acta 1989, 72, 1416.
7. Abou-Gharbia, M.; Moyer, J. A.; Patel, U.; Webb, M.; Schiehser, G.; Andree, T.; Haskins, J. T. J. Med. Chem. 1989, 23, 1024.
8. Schulze, B.; Kirsten, G.; Kirrbach, S.; Rahm, A.; Heimgärtner, H. Helv. Chim. Acta 1991, 74, 1059.
9. (a) Marco, J. L.; Ingate, S. T. Tetrahedron Lett. 1997, 38, 4835.
10. (b) Ingate, S. T.; Marco, J. L.; Witvrouw, M.; Pennecouque, C.; De Clerq, E. Tetrahedron 1997, 53, 17795.
11. (c) Marco, J. L.; Ingate, S. T. Tetrahedron Lett. 1998, 39, 4123.
12. (d) Marco, J. L.; Ingate, S. T.; Chinon, P. M. Tetrahedron 1999, 55, 7625.
13. (e) Marco, J. L.; Ingate, S. T.; Jaime, C.; Bea, J. Tetrahedron 2000, 56, 2523.
14. Fischer, R.; Kretschik, O.; Schenke, T.; Schenkel, R.; Wiedemann, J.; Erdelen, C.; Loesel, P.; Drewes, M. W.; Feucht, D.; Andersen, W. Ger. Offen. DE 1999244668, 1999; Chem. Abstr. 2001, 134, 4932.
15. Hanson, P. R.; Probst, D. A.; Robinson, R. E.; Yan, M. Tetrahedron Lett. 1999, 40, 4761.
16. Ho, K. F.; Fung, D. C. W.; Wong, W. Y.; Chan, W. H.; Lee, A. W. M. Tetrahedron Lett. 2001, 42, 3121.
17. Wanner, J.; Harned, A. M.; Probst, D. A.; Poon, K. W. C.; Klein, T. A.; Snelgrove, K. A.; Hanson, P. R. Tetrahedron Lett. 2002, 43, 917.
18. Taubert, K.; Sieler, J.; Hennig, L.; Findeisen, M.; Schulze, B. Helv. Chim. Acta 2002, 85, 183.
19. Gelalcha, F. G.; Schulze, B. J. Org. Chem. 2002, 67, 8400.
20. Baumann, S.; Möder, M.; Herzschuh, R.; Schulze, B. Chromatographia 2003, 57, S147.
21. Gütschow, M.; Pietsch, M.; Taubert, K.; Freysoldt, T. H. E.; Schulze, B. Z. Naturforsch., B: Chem. Sci. 2003, 58, 111.
22. Armstrong, A.; Barsanti, P. A.; Clarke, P. A.; Wood, A. J. Chem. Soc., Perkin Trans. 1 1996, 1373.
23. Schulze, B.; Taubert, K.; Gelalcha, F. G.; Hartung, C.; Sieler, J. Z. Naturforsch., B: Chem. Sci. 2002, 57, 383.
24. 22 Crystallographic data for the structural analyses have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 217553 for 15f. Copies of the data can be obtained, free of charge, from CCDC, 12 Union Road, Cambridge, CB2 1EZ. UK (fax:+44(1233)336033; e-mail: deposit@ccdc.cam.ac.uk; internet: http:// www.ccdc.cam.ac.uk).
25. Sheldrick, G. M. Acta Cryst. 1990, 46, 467.
26. Sheldrick, G. M. SHELXL-97, Program for the refinement of crystal structures; Göttingen: Germany, 1997.