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Tytuł artykułu

Synthesis of N-Unsubstituted 1,3-Thiazollidines by [2+3]-Cycloaddition of an Azomethine Ylide with Thiocarbonyl Compounds

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
1,3-Dipolar cycloadditions of azomethine ylides with thiocarbonyl compounds have been used for the preparation of N-unsubstituted 1,3-thiazolidines. The reactive 1- phenyl-N-(trimethylsilyl)azomethine ylide (1c) was generated in situ by treatment of N-(benzylidene)[(trimethylsilyl)methyl]amine (6) with trimethylsilyl triflate and CsF in HMPA. All cycloadditions proceeded non-regioselectively, which led to mixtures of 4-phenyl- and 2-phenyl-substituted 1,3-thiazolidines.
Rocznik
Strony
157--167
Opis fizyczny
Bibliogr. 41 poz., rys.
Twórcy
autor
  • Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
autor
  • Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
autor
  • Section of Heteroorganic Compounds, University of Łódź, Narutowicza 68, PL-90-136 Łódź, Poland
  • Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
Bibliografia
  • 1. Lown J.W., in “1,3-Dipolar Cycloaddition Chemistry”, ed. Padwa A., Wiley-Interscience, NY, 191 Vol. 1, p. 653.
  • 2. Vedejs E., Adv. Cycloaddition, 1, 33 (1988).
  • 3. Terao Y., Aono M. and Achiwa K., Heterocycles, 27, 981 ( 1988).
  • 4. Padwa A., in “Comprehensive Organic Synthesis”, eds., Trost B.M. and Fleming I., Pergamon Prt Oxford, 1991, Vol. 4, p. 1085; Wade P.A., ibid., p. 1134.
  • 5. Grigg R. and Sridharan V., Adv. Cycloaddition, 3,161 (1993).
  • 6. Harwood L.M. and Vickers R.J., in “Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry ward Heterocycles and Natural Products”, eds. Padwa A. and Pearson W.H., J. Wiley & Sons, NY, 20 p. 169.
  • 7. Clark J.S., in “Nitrogen, Oxygen and Sulfur Ylide Chemistry, A Practical Approach”, ed. Clark J.S., ( ford University Press, 2002, p. 57.
  • 8. Merino I., Santosh Laxmi Y.R., Florez J., Barluenga J., Ezquerra J. and Pedregal C., J. Org. Chem., 648 (2002); Garcia Ruano J.L., Tito A. and Peromingo M.T., ibid., 67, 981 (2002).
  • 9. Huisgen R., Funke E., Schaefer F.C. and Knorr R, Angew. Chem. Int. Ed., 6, 367 (1967).
  • 10. Lown J.W., Dallas G. and Maloney T.W., Can. J. Chem., 47,3557 (1969); Lown J.W., Maloney T.W.i Dallas G., ibid., 48. 584 (1970); Lown J.W. and Matsumoto K„ ibid., 48, 3399 (1970).
  • 11. Huisgen R., Martin-Ramos V. and Scheer W., Tetrahedron Lett., All (1971).
  • 12. Beugelmans R., Chastanet J. and Roussi G., Heterocycles, 26, 3197 (1987).
  • 13. Padwa A. and Dent W., J. Org. Chem., 52, 235 (1987).
  • 14. Planchenault D., Wisedale R., Gallagher T. and Hales N.J., J. Org. Chem., 62, 3438 (1997).
  • 15. Gallagher T.,J. Heterocycl. Chem., 36, 1365 (1999).
  • 16. Mlostoń G. and Skrzypek Z., Bull. Soc. Chim. Belg., 99, 167 (1990).
  • 17. Mlostoń G., Linden A. and Heimgartner H., Polish J. Chem., 71, 32 (1997); Helv. Chim. Acta, 81, (1998).
  • 18. Gebert A., Linden A., Mlostoń G. and Heimgartner H., Heterocycles, 56, 393 (2002).
  • 19. Mlostoń G., Urbaniak K. and Heimgartner H., Helv. Chim. Acta, 85, 2056 (2002).
  • 20. Mlostoń G., Urbaniak K., Linden A. and Heimgartner H., Helv. Chim. Acta, 85, 2644 (2002).
  • 21. Gebert A., Linden A. and Heimgartner H., Heterocycles, 54, 691 (2001 ).
  • 22. Gebert A. and Heimgartner H., Helv. Chim. Acta, 85, 2073 (2002).
  • 23. Achiwa K. and Sckiya M., Tetrahedron Lett., 23, 2589 (1982).
  • 24. Tsuge O., Kanemasa S. and Matsuda K., Chem. IeK.,1131 (1983); Tsuge O., Kanemasa S., Hatad; and Matsuda K., ibid, 801 (1984).
  • 25. Johnson C.K., “ORTEPII”, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tem see, 1976.
  • 26. Huisgen R. and Langhals E., Tetrahedron Lett., 30, 5369 (1989); Huisgen R., Fisera L.. Giera H. Sustmann R., J. Am. Chem. Soc., 117, 9678 (1995).
  • 27. Obrecht D., Prewo R., Bieri J.H. and Heimgartner H., Helv. Chim. Acta, 65, 1825 (1982); Jenny C. Heimgartner H., ibid, 69, 374 (1986).
  • 28. Tromm P. and Heimgartner H., Helv. Chim. Acta, 71, 2071 (1988).
  • 29. Pedersen B.S., ScheibyeS.,NilssonN.H. andLawesson S.-O., Bull. Soc. Chim. Belg., 87,233 (1978)
  • 30. Mlostoń G., Celeda M., Rocsky H.W., Parisini E. and Ahlemann J.-T., Eur. J. Org. Chem., 459 (1998)
  • 31. Mlostoń G., Romański J., Linden A. and Heimgartner H., Helv. Chim. Acta. 16, 2147 (1993).
  • 32. Lettelier M., McPhee D.J. and Griller D., Synth. Commun., 18, 1975 (1988).
  • 33. Sheldrick G.M., SHELXS86, Acta Crystallogr., Sect. A, 46, 467 (1990).
  • 34. Altomare A., Cascarano G., Giacovazzo C., Guagliardi A., Burla M.C., Polidori G. and Camalli SIR92, J. Appl. Crystallogr., 27, 435 (1994).
  • 35. Le Page Y„ J. Appl. Crystallogr., 20, 264 (1987); ibid., 21, 983 (1988).
  • 36. Spek A.L., Acta Crystallogr., Sect. A, 46, C31 (1990).
  • 37. 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 6.1.1.1, 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.
  • 38. Stewart R.F., Davidson E.R. and Simpson W.T., J. Chem. Phys., 42, 3175 (1965).
  • 39. Ibers J.A. and Hamilton W.C., Acta Crystallogr., 17, 781 (1964).
  • 40. TEXSAN: Single Crystal Structure Analysis Software, Version 5.0, Molecular Structure Corporation, The Woodlands, Texas, 1989.
  • 41. teXsan: Single Crystal Structure Analysis Software, Version 1.10b, Molecular Structure Corporation, The Woodlands, Texas, 1999.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0023-0075
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