Reactions of Thioesters with Organic Azides-A Novel Accesss to Imidates and Thioimidates

• Autorzy: Mlostoń G. , Romański J. , Heimgartner H.
• Języki publikacji: EN

Abstrakty

EN

The reaction of O-methyl thiocarboxylates 8a, b with organic azides at 110_C yielded the corresponding imidates of type 9, which were easily hydrolyzed to give amides 10. The formation of 9 can be rationalized by a 1,3-dipolar cycloaddition of the azide with the C=S group, followed by the "twofold extrusion" ofN2 and S. The analogous reaction with methyl dithiobenzoate (11) led to thioimidates 13. On heating, the latter were transformed into thioamides 12.

Słowa kluczowe

EN

1,3-dipolar cycloadditions; twofold extrusion; thioesters; organic azides; thiaziridines

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2001
• Tom: Vol. 75, nr 7
• Strony: 975--982
• Opis fizyczny: Bibliogr. 36 poz., rys.

Twórcy

autor

Mlostoń G.

• Section of Heteroorganic Compounds, University of Lódź, Narutowicza 68, PL-90-136 Lódź, Poland

autor

Romański J.

• Section of Heteroorganic Compounds, University of Lódź, Narutowicza 68, PL-90-136 Lódź, Poland

autor

Heimgartner H.

• Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

Bibliografia

• 1.Heimgartner H., Phosporus, Sulfur and Silicon, 58, 281 (1991).
• 2.Mlostoń G., Romański J., Kagi M. and Heimgartner H., Polish J. Appl. Chem., 41, 361 (1997).
• 3.Mlostoń G., Phosphorus, Sulfur and Silicon, 153, 217 (1999).
• 4.Mlostoń G. and Heimgartner H., Polish J. Chem., 74, 1503 (2000).
• 5.Mlostoń G., Romański J., Linden A. and Heimgartner H., Polish J. Chem., 70, 880 (1996).
• 6.Mlostoń G., Romański J., Linden A. and Heimgartner H., Helv. Chim. Acta, 78, 1067 (1995).
• 7.Fabian J. and Mlostoń G., Polish J. Chem., 73, 669 (1999); Mlostoń G. and Fabian J., Polish J. Chem., 683 (1999).
• 8.Schónberg A. and Urban W., J. Chem. Soc., 530 (1935).
• 9.Guziec F.S. and Moustakis Ch., J. Chem. Soc., Chem. Commun., 63 (1984).
• 10.Pekcan S. and Heimgartner H., Helv Chim. Acta, 71, 1673 (1988).
• 11.Metzner P., Topics Curr. Chem., 204, 127 (1999).
• 12.Huisgen R. and Li X., Tetrahedron Lett., 24, 4185 (1983).
• 13.Mlostoń G., Romański J., Linden A. and Heimgartner H., Helv. Chim. Acta, 78, 1499 (1995).
• 14.Mlostoń G., Chem. Papers, 52, 56 (1998).
• 15.Guziec F.S. and Sanfilippo L.J., Tetrahedron, 44, 6241 (1988).
• 16.Bachi M.D. and Rothfield M., J. Chem. Soc., Perkin Trans. 1, 2326 (1972).
• 17.Walter W. and Meese C.O., Chem. Ber., 109, 922 (1976).
• 18.Depczynski R., Diploma thesis, University of Łódź, 2000.
• 19.a) Pielartzik H., Irmisch-Pielartzik B. and Eicher T., in “Methoden der organischen Chemie (Houben- Weyl)”, Band E5/1, ed. Falbe J., Thieme Verlag, Stuttgart, 1985, p. 812; b) Bauer W. and Kiihlein K., ibid., Band E5/2, p. 931.
• 20.Bellassoued M., Gaudemar M., Hajjem B. and Baccar B., Bull. Soc. Chim. Belg., 95, 65 (1986).
• 21.Padwa A., Gasdaska J.R., Hoffmann G. and Rebelio H., J. Org. Chem., 52, 1027 (1987).
• 22.Schulthess A.H. and Hansen H.-J., Helv. Chim. Acta, 64, 1322 (1981).
• 23.Hiroi K, Hidaka A., Sesaki R. and Iwamura Y., Chem. Pharm. Bull. Jpn., 45, 769 (1997).
• 24.Ugi I., Perlinger H. and Behringer L., Chem. Ber., 91, 2330 (1958).
• 25.MaierG., Eckwert J., Bothur A., Reisenauer H.P. and Schmidt Ch., Liebigs Ann. Chem., 1041 (1996).
• 26.Pedersen B.S., Scheibye S., Clausen K. and Lawesson S.-O., Bull. Soc. Chim. Belg., 87, 293 (1978).
• 27.Davy H., J. Chem. Soc., Chem. Commun., 457 (1982).
• 28.Mayer R., Scheithauer S. and Kunz D., Chem. Ber., 99, 1393 (1966).
• 29.Supniewski J., Preparation of Inorganic Compounds, PWN, Warszawa 1958, p. 412 (in Polish).
• 30.Raap R., Can. J. Chem., 49, 1792 (1971).
• 31.Metz P. and Mues C., Tetrahedron, 44, 6841 (1988).
• 32.Knowles H.S., Parson A.F., Pettiter R.M. and Rickling S., Tetrahedron, 56, 979 (2000).
• 33.Williams A., Lucas E.C., Rimmer A.R. and Hawkins H.C., J. Chem. Soc., Perkin Trans. 2, 627 (1972).
• 34.De Bruin K.E. and Boros E.E., J. Org. Chem., 55, 6091 (1990).
• 35.Boudet R.,Ann. Chim. (Paris), 10, 178 (1955); Chem. Abstr., 50, 4055a (1956).
• 36.Sasaki Y. and Olsen F.P., Can. J. Chem., 49, 271 (1971).