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

Gebert, A.; Linden, A.; Mlostoń, G.; Heimgartner, H.

Artykuł - szczegóły

Tytuł artykułu

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

Autorzy

Gebert A. , Linden A. , Mlostoń G. , Heimgartner H.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

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.

Słowa kluczowe

azomethine ylides 1,3-dipolar cycloadditions thiocarbonyl ylides 1,3 thiazolidines crystal structure

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Polish Journal of Chemistry

Rocznik

2003

Tom

Vol. 77 / nr 2

Strony

157--167

Opis fizyczny

Bibliogr. 41 poz., rys.

Twórcy

autor

Gebert A.

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

autor

Linden A.

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

autor

Mlostoń G.

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

autor

Heimgartner H.

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