Browse > Article

Oxidation of Pyridazinyl Sulfides: Synthesis of New Pyridazinyl Sulfoxides and Pyridazinyl Sulfones with Aqueous Hydrogen Peroxide  

Park, Eun-Hee (College of Pharmacy, Duksung Women's University)
Park, Myung-Sook (College of Pharmacy, Duksung Women's University)
Publication Information
YAKHAK HOEJI / v.56, no.6, 2012 , pp. 390-394 More about this Journal
Abstract
A series of new pyridazinyl sulfoxides 3a~e and pyridazinyl sulfones 4a were synthesized for development of candidates to retain anticancer activity. The utility of sulfoxides and sulfones in both laboratory and industrial practice was quickly recognized, and these species have been extensively utilized, including as pharmaceutical intermediates and anticancer agents. Alkylthiopyridazines 2a~e were prepared from the 3,6-dichloropyridazine using allylthiolation with alkyl mercaptan. Sulfides could be oxidized to sulfoxides or sulfones using 1~3 equivalents of hydrogen peroxide as an oxidant. The oxidation of sulfoxides to sulfones was also accomplished with aqueous hydrogen peroxide. Formation of 3a~e and 4a was undertaken with stirring using 35% hydrogen peroxide at room temperature in acetic acid for 18~72 h. Synthetic compounds were identified using NMR spectrum.
Keywords
pyridazinyl sulfides; pyridazinyl sulfoxides; pyridazinyl sulfones; oxidation; hydrogen peroxide;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Goodman and Gilman's The Pharmacological Basis fo Ther-apeutics, 12th, McGraw-Hill com., Inc., pp. 1737-1738 (2011).
2 Moy, B. and Goss, P. E. : Lapatinib-associated toxicity and practical management recommendations. Oncologist 12, 756 (2007).   DOI   ScienceOn
3 Geyer, C. E., Forster, J., Lindquist, D., er al. : Lapatinib plus capecitabine for HER2-positive advanced breast cancer. N Engl. J. Med. 355, 2733 (2006).   DOI
4 Tarbell, D. S. and Weaver, C. : The condensation of sulfoxides with p-toluenesulfonamide and substituted acetamides. J. Am. Chem. Soc. 63, 2939 (1941).   DOI
5 Smith, M. B. and March, J. : March's Advanced Organic Chemistry, 6th, Wiley & Sones, Inc., pp. 1780-1784 (2007).
6 Edwards, D. and Stenlake, J. B. : The oxidation of alkyl sulphides. J. Chem. Soc. 63, 3272 (1954).
7 Trost, B. M. and Curran, D. P. : Chemoselective oxidation of sulfides to sulfones with potassium hydrogen persulfate. Tetrahedron Lett. 22, 1287 (1981).   DOI   ScienceOn
8 Trost, B. M. and Braslau, R. : Tetra-n-butylammonium oxone. Oxidations under anhydrous conditions. J. Org. Chem. 53, 532 (1988).   DOI
9 Raju, B. R., Sarkar, S., Reddy, U. C. and Saikia, A. K. : Cerium (IV) triflate-catalyzed selective oxidation of sulfides to sulfoxides with aqueous hydrogen peroxide. J. Molecul. Catal. A, Chem. 308, 169 (2009).   DOI   ScienceOn
10 Romanelli, G. P., Villabrille, P., Caceres, C. V., Vazquez, P. G. and Tundo, P. : Keggin heteropolycompounds as catalysts for liquid-phase oxidation of sulfides to sulfoxides/sulfones by hydrogen peroxide. Catal. Comm. 12, 726 (2011).   DOI   ScienceOn
11 Gregori, F., Nobili, I., Bigi, F., Maggi, R. and Predieri, G. : Selective oxidation of sulfides to sulfoxides and sulfones using 30% aqueous hydrogen peroxide and silica-vanadia catalyst. J. Molecul. Catal. A, Chem. 286, 124 (2008).   DOI   ScienceOn
12 Hudlicky, M. : Oxidation in Organic Chemistry, American Chemical Society, Washington, DC, pp. 252-263 (1990).
13 Venier, C. G., Squires, T. G., Chen, Y. Y., Hussmann, G. P., Shei, J. C. and Smith, B. F. : Peroxytrifluoroacetic acid. A convenient reagent for the preparation of sulfoxides and sulfones. J. Org. Chem. 47, 3773 (1982).   DOI
14 Paquette, L. A. and Carr, R. V. C. : Phenyl vinyl sulfone and sulfoxide. Org. Synth. 64, 157 (1986).   DOI
15 Laba, V. I., Sviridova, A. V. and Prilezhaeva, E. N. : Synthesis of acetylenic sulfoxides. Bull. Aca. Sci. USSR 21, 213 (1972).   DOI   ScienceOn