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Abstrakty
Reactions of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (1, ‘cage’ dione) with primary amines (i.e. benzylamine, aniline, methylamine and 2-aminoethanol) leading to the adducts 4a–d in good yields are described. In all cases the transannular cyclization process was observed and oxa-bridged products 4a–d were obtained. Isolated compounds were identified as hemiacetals or their internal salts. The type of the formed product is dependent on basicity of the used amines. Subsequent dehydration of the initially obtained adducts in boiling benzene led to monoimines 3a–d..
Słowa kluczowe
Wydawca
Czasopismo
Rocznik
Tom
Strony
187--191
Opis fizyczny
Bibliogr.8 poz., rys.
Twórcy
autor
- University of Łódź, Department of Organic and Applied Chemistry, Section of Heteroorganic Compounds, Narutowicza 68, 90-136Łódź, Poland
Bibliografia
- 1.Marchand A.P., Aldrichimica Acta, 28, 95 (1995) and references cited therein.
- 2.Smith M.B. and March J., March s Advanced Organic Chemistry; 5th Ed.; John Wiley & Sons: New York 2001 ;pp. 1185-1187.
- 3.Crank G., Szinai S.S. and Harding D.R.K., J. Med. Chem., 13,1215 (1970); Shinya S. and Ishikawa N., Bull. Chem. Soc. Jpn., 50, 329 (1977).
- 4.Cookson R.C., Grundwell E., Hill R.R. and Hudec J., J. Chem. Soc., 3062 (1964).
- 5.Sasaki T., Eguchi S., Kiriyama T. and Hiroaki O., Tetrahedron, 30, 2707 (1974).
- 6.Romański J. and Mlostoń G., Synthesis, 1644 (2002); Romański J. and Marchand A.P., Polish J. Chem., 78, 223 (2004); Linden A., Romański J., Mlostoń G. and Heimgartner H., Acta Crytstallogr. Sect. C, C61,221(2005).
- 7.Marchand A.P., Arney B.E., Dave P.R., Satyanarayana N., Watson W.H. and Nagl A., J. Org. Chem., 53, 2644 (1988); Malan S.F., Van der Walt J.J. and Van der Schyf C.J., Arch. Pharm. Pharm. Med. Chem.,333,10(2000).
- 8.Liebenberg W., Van der Walt J.J. and Van der Schyf C.J., Pharmazie, 55, 833 (2000).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ5-0008-0025