A novel one-pot synthesis of derivatives of aryldioxins and aryldithiins

Tetrahedron Letters

Volumn 45, Issue 7, 2004, Pages 1343-1346

  Preedasuriyachai, Patcharee ^a   Charoonniyomporn, Porntip ^a   Karoonnirun, Osit ^a   Thongpanchang, Tienthong ^a   Thebtaranonth, Yodhathai ^a  

^a MAHIDOL UNIVERSITY   (Thailand)

Author keywords

Arylsulfide; Dioxin; Dithiin; Heterocyclic compounds; Tautomerization

Indexed keywords

1,2 ETHANEDITHIOL; 2,3 NAPHTHALENEDIOL; 2,3 NAPHTHODIOXIN; 9,10 PHENANTHRODIOXIN; DIOXIN; DITHIOL DERIVATIVE; NAPHTHALENE DERIVATIVE; PHENANTHRENE DERIVATIVE; SULFONIC ACID DERIVATIVE; TOLUENE; TOLUENESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0942298968     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.069     Document Type: Article

References (37)

1. Palmer B.D., Rewcastle G.W., Artwell G.J., Baguley B.C., Denny W.A. J. Med. Chem. 31:1988;707-712.
2. Lee H.H., Palmer B.D., Boyd M., Baguley B.C., Denny W.A. J. Med. Chem. 35:1992;258-266.
3. Ruiz N., Boun C., Pukol M.D., Guillaumet G., Coudert G. Synth. Commun. 26:1996;2057-2066.
4. Fagan G.P., Chapleo C.P., Lane A.C., Meyers M., Roach A.G., Roach C.F.C., Stillings M.R., Welbourn A.P. J. Med. Chem. 31:1988;944-948.
5. Guaglia W., Pigini M., Tabeyati S.K., Piergentili A., Giannella M., Leonardi A., Taddei C., Melchiorre C. J. Med. Chem. 39:1996;2253-2258.
6. Ruffolo R.R., Bondinell W. Jr., Hieble J.P. J. Med. Chem. 38:1995;3681-3716.
7. Marciniak G., Delgado A., Lederc G., Velley J., Decker N., Schwartz J. J. Med. Chem. 32:1989;1402-1407.
8. Nelson W.L., Wennerstrom J.E., Dyer D.C., Engel M. J. Med. Chem. 20:1977;880-885.
9. Hellberg J., Pelcman M.E. Tetrahedron Lett. 35:1994;1769-1772.
10. Czekanski T., Hanack M., Becker J.Y., Bernstein J., Bittner S., Kaufman-Orenstein L., Peleg D. J. Org. Chem. 56:1991;1569-1573.
11. Tomita M., Ueda S., Nakai Y., Deguchi Y., Takaki H. Tetrahedron Lett. 4:1963;1189-1194.
12. Clavier S., Kouili M., Bouyssou P., Coudert G. Tetrahedron. 58:2002;1533-1540.
13. Delgado A., Lerlerc G.M., Lobato C., Mauleon D. Tetrahedron Lett. 29:1988;3671-3674.
14. Labrosse J.R., Lhoste P., Sinou D. Tetrahedron Lett. 40:1999;9025-9028.
15. Massacret M., Lakhmiri R., Lhoste P., Nguefack C., Ben Abdelouahab F.B., Fadel R., Sinou D. Tetrahedron: Asymmetry. 11:2000;3561-3568.
16. Chowdhury C., Chaudhuri G., Guha S., Mukherjee A.K., Kundu N.G. J. Org. Chem. 63:1998;1863-1871.
17. Massacret M., Goux C., Lhoste P., Sinou D. Tetrahedron Lett. 35:1994;6093-6096.
18. Anjaneyulu B., Govindachari T.R., Viswanathan N. Tetrahedron. 27:1971;439-443.
19. Kende A.S., Wade J.J., Ridge D., Poland A. J. Org. Chem. 39:1974;931-937.
20. Gilman H., Dietrich J.J. J. Am. Chem. Soc. 79:1957;1439-1441.
21. Lee H.H., Denny W.A. J. Chem. Soc., Perkin Trans. 1. 1990;1071-1074. and references cited therein.
22. Eastmond G.C., Paprotny J. Chem. Lett. 1999;479-480.
23. Gray A.P., Cepa S.P., Solomon I.J., Aniline O. J. Org. Chem. 41:1976;2435-2437.
24. Sutherland R.G., Piorko A., Lee C.C., Simonsen S.H., Lynch V.M. J. Heterocycl. Chem. 25:1988;1911-1916.
25. For example, thianthrene was incorporated, as electron donor, in charge transfer complexation. Rainville D.P., Zingaro R.A., Ferraris J.P. Can. J. Chem. 58:1980;1133-1137.
26. Gilman H., Stuckwisch C.G. J. Am. Chem. Soc. 65:1943;1461-1464.
27. Caputo R., Ferreri C., Palumbo G., Russo F. Tetrahedron. 47:1991;4187-4194.
28. Alcaide B., Plumet J., Rodriguez-Campos I.M. Heterocycles. 24:1986;141-142.
29. Charoonniyomporn P., Wittayakran S., Thongpanchang T., Thebtaranonth Y., Katz T.J., Phillips K.E.S. Tetrahedron Lett. 45:2004;457-459.
30. 3.
31. When 1,3-propanedithiol was reacted with 2,3-dihydroxynaphthalene under the same reaction conditions, only 2,3-bis(1-propylthio)naphthalene was formed exclusively. Wittayakran, S.; Thongpanchang, T. Unpublished results.
32. abstract
33. Dreher S.D., Paruch K., Katz T.J. J. Org. Chem. 65:2000;806-814.
34. footnotes 5-10 therein.
35. Dreher S.D., Katz T.J., Lam K.C., Rheingold A.L. J. Org. Chem. 65:2000;815-822.
36. Drake N.L. Org. React. 1:1942;105-128.
37. Seeboth H. Angew. Chem., Int. Ed. Engl. 6:1967;307-317.