Ambivalent Nucleophilicity of 1,4,5-Trisubstituted Imidazole-2-thiones in Reactions with Dimethyl Acetylenedicarboxylate and Phenylisocyanate

• Autorzy: Mlostoń G. , Gendek T. , Linden A. , Heimgartner H.
• Języki publikacji: EN

Abstrakty

EN

The 1,4,5-trisubstitued 2,3-dihydro-1H-imidazole-2-thiones 1 react with electrophilic re agents via the S- or the N(3)-atom. The reaction with dimethyl acetylenedicarboxylate in methanol at room temperature occurs by the nucleophilic addition of the S-atom to give the corresponding 2-[(1H-imidazol-2-yl)sulfanyl]fumarates 4 in high yield. On the other hand, imidazole-2-thiones 1 react with phenylisocyanate in dichloromethane at room temperature to yield 2,3-dihydro-2-thioxo-1H-imidazole-1-carboxamides 5. The structures of both types of adducts were established by X-ray crystallography.

Słowa kluczowe

EN

imidazole-2-thiones; addition reactions; acetylenedicarboxylates; isocyanates; X-ray crystallography

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2008
• Tom: Vol. 82, nr 8
• Strony: 1561--1561
• Opis fizyczny: –1569, Bibliogr. 27 poz., rys.

Twórcy

autor

Mlostoń G.

autor

Gendek T.

autor

Linden A.

autor

Heimgartner H.

• Department of Organic and Applied Chemistry, University of Łódź Narutowicza 68, PL-90-136 Łódź, Poland,

Bibliografia

• 1. Trzhtsinskaya B.V. and Abramova N.D., Sulfur Rep., 10, 389 (1991).
• 2. Bartnik R., Hann W.E. and Mlostoń G., Roczniki Chem., 51,49 (1977); Chem. Abstr., 87,53155g (l977).
• 3. Mlostoń G., Jasiński M., Linden A. and Heimgartner H., Helv. Chim. Acta, 89, 1304 (2006).
• 4. Jasiński M., Mlostoń G., Mucha R, Linden A. and Heimgartner H., Helv. Chim. Acta, 90,1765 (2007).
• 5. a) Ross S.T., Kruse L.I., Ohlstein E.H., Erickson R.W., Ezekiel M., Flaim K.E., Saweyer J.L. and Berkowitz B.A., J. Med. Chem. ,30, 1309 (1987); b) Trzhtsinskaya B. V., Aleksandrova A.E., Abramova N.D., Andriyankova L.V., Vinogradova T.I. and Shchegoleva R.A., Khim.-Farm. Zh., (at present: Pharm. Chem. J.), 16, 122 (1982); c) Wagner G. and Laufer S., Med. Res. Rev., 26,l (2006).
• 6. a) Laufer S., Wagner G. and Kotschenreuther D., Angew. Chem., Int. Ed.,41,2290 (2002); b) Theoclitou M.-E., DelaetN.G.J. and Robinson L.A., J. Comb. Chem., 4, 315 (2002); c) Laufer S.A., Wagner G.K., Kotschenreuther D.D. and Albrecht W, J. Med. Chem., 46, 3230 (2003); d) Loksha Y.M., El-Barbary A.A., El-Badawi M.A., Nielsen C. and Pedersen E.B., Bioorg. Med. Chem., 13, 4209 (2005).
• 7. Acheson R.M. and Wallis J.D., J. Chem. Soc., Perkin Trans, 1, 415 (1981).
• 8. Yavari L, Alizadeh A. and Anary-Abbasine M., Phosphorus, Sulfur, Silicon, and Relat. Elem., 178,269 (2003); b) Maghsoodlou M.T., Hazeri N., Khorassani S.M.H., Nassiri M., Marandi G., Afshari G. and Niroumand U., J. Sulfur Chem., 26, 261 (2005).
• 9. For example, see in: Laue T, Plagens A., 'Named Organic Reactions', J. Wiley & Sons, Chichester, 1998, p. 192.
• 10. Skvortsova G.G., AbramovaN.D., Malkina A.G., Skvortsov Yu.M., Trzhtsinskaya B.V. and Abramova A.T., Khim. Geterotsikl. Soedin., 963 (1982).
• 11. Mlostoń G., Gendek T. and Heimgartner H., Helv. Chim. Acta, 81, 1585 (1998).
• 12. Kaydos J.A. and Smith D.L., J. Org. Chem. 48, 1096 (1983).
• 13. Johnson C.K., ORTEPII. Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
• 14. a) Tittelbach F. and Martin D., J. Prakt. Chem., 330,338 (l 988); b) Martin D. and Tittelback F., Tetrahedron,39,2311 (1983).
• 15. a) Koketsu M., Kobayashi C. and Ishihara H., Heteroatom Chem., 14,374 (2003); b) Mizuno T, Iwai T. and Ishino Y, Tetrahedron, 61, 9157 (2005).
• 16. Dyer E. and Minnier C.E., J. Heterocycl. Chem., 6, 23 (1969).
• 17. BernsteinJ., Davis R.E., Shimoni L. and Chang N.-L., Angew. Chem. Int. Ed. Engl.,34, 1555 (1995).
• 18. Hooft R., KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
• 19. Otwinowski Z. and Minor W, in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography', Part A, Eds. Carter C. W, Jr. and Sweet R.M., Academic Press, New York, 1997, p. 307.
• 20. Blessing R.H., Acta Crystallogr., Sect. A, 51, 33 (1995).
• 21. Altomare A., Cascarano G., Giacovazzo C., Guagliardi A., Burla M.C., Polidori G. and Camalli M.,SIR92, J. Appl. Crystallogr., 27, 435 (l994).
• 22. Spek A.L., PLATON, Program for the Analysis of Molecular Geometry. University of Utrecht, The Netherlands, 2008.
• 23. a) Flack H.D. and Bernardinelli G., Acta Crystallogr., Sect. A, 55, 908 (1999); b) Flack H.D. and Bernardinelli G., J. Appl. Crystallogr., 33, 1143 (2000).
• 24. a) Maslen E.N., Fox A.G. and O'Keefe M.A., in * International Tables for Crystallography', Ed. Wilson A.J.C., Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 6. l. l. l, p. 477; b) Creagh D.C. and McAuley W.J., ibid., Table 4.2.6.8, p. 219; c) Creagh D.C. and Hubbell J.H., ibid., Table 4.2.4.3, p. 200.
• 25. Stewart R.F., Davidson E.R. and Simpson W.T., J. Chem. Phys., 42, 3175 (1965).
• 26. Ibers J.A. and Hamilton W.C., Acta Crystallogr., 17, 781 (1964).
• 27. Sheldrick G.M., SHELXL 97, Program for the Refmement of Crystal Structures, University of Góttingen, Germany, 1997.