A route to pyrrolizidines, indolizidines and quinolizidines via intramolecular oxime olefin cycloadditions

Alfred Hassner, Rakesh Maurya

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41 Scopus citations

Abstract

A route to functionalized pyrrolizidines, indolizidines or quinolizidines is described. The reaction involves thermal cycloaddition of pyrrolidines or piperidines, possessing properly positioned aldoxime and alkene functions, and proceeds with stereospecific introduction of three stereo centers.

Original languageEnglish
Pages (from-to)2289-2292
Number of pages4
JournalTetrahedron Letters
Volume30
Issue number17
DOIs
StatePublished - 1989

Bibliographical note

Funding Information:
2.5 Hz), 2.67 (dt, H-b, J= 10.5, 7 Hz), 2.24 (m, llf), 1.8-2.0 (m, 3H). '=C-NMR (CDCl=, at 75 MHz): 24.67 (t), 29.61 (t), 46.31 (d, C-H=), 53.44 (t, C-51, 57.20 (t, C-6), 67.79 (d, C-Hb), 71.99 (d, C-H,), 74.67 (t, C-71, 127.90, 129.28, 131.43, 132.98 (arom C), 169.45 (C=O). Mass spectra CI~H=~N~O~.M W 258 m/e (%l: 259 (12%, MH'), 257 (2%, M-l), 228 (26%), 173 (23%), 153 (9%k), 151 (8.5%), 123 (84%, M-PhCONO), 108 (87%), 105 (loo%), 83 (60.5%). Acknowledgerent: Support of this research by a grant from the United States - Israel Binational Science Foundation is greatfully acknowledged. References 1. Synthetic methods 30. For paper 29 see Hassner A., Rai, K.M.L. Synthesis (19891, 57. 2. Kametani, T., Huang, S.D., Nakayama, A., Hondu, T. J.Orn.Chem., (1982) 47, 2328; Tufariello, J. in "1,3-Dipolar Cycloaddition Chemistry", Padwa, A. Ed. Wiley-Interscience, New York, Vol 2, (19841; Tufariello, J. Act. Chem. Res. (1979) l2, 396. Oppolzer, W. Ansew. Chem. Int. Hd. (1977) l6, 10; Wovkulich, P.M., Uskokovic, M. J.Amer.Chem.Soc. (1981) 103, 3956. 3. a) Grigg, R., Jordan, M., Tangthongkum, A., Einstein, F.W.H., Jones,T. J.Chem.Soc. Perkin Trans I 11984) 47; Armstrong, P., Grigg, R., Warnock, W.J. J.Chem.Soc. Chem.Commun. (1987) 1325; Grigg, R., Malone, J.F., Dorrity, M.R.J., Heaney, F., Rajviroongit, S., Sridharan, V., Surendrakumar, S. Tetrahedron Lett., (19881, 29, 4323; b) Grigg, Chem.Soc.Rev. (1987) l6, 89. Grigg, R., Thianpantangul, S. J.Chem.Soc. Perkin Trans. I (1984) 653. 4. Padwa, A., Norman, B.H. Tetrahedron Lett. (1988) 29, 2417 5. Oppolzer, W., Keller, K. Tetrahedron Lett. (1970) 1117; Heathcock, C.H., Norman, M.H. J.Org.Chem. (19871, 52, 226. 6. Hassner, A., Maurya, R, Mesko, E. Tetrahedron Lett. (19881, 29, 5313. 7. For some recent references see Ikeda, M., Sato, T., Ishibashi, H. Heterocvcles, (1988),27, 1465; Zeller, E., Grierson ibid (19881, 22, 1575; Gribble, G.W., Switzer, F.L., Soll, R.M. J. Org. Chem. (19881 53, 3164; Grieco, P.A., Parker, D.T. ibid, (1988), 53, 3325; Tokuyama, T., Nishimori, N., Shimada, A. Tetrahedron (1987), 43, 643 8. At 200-C a considerable amount of decomposition occured. 9. Hassner, A., Murthy, K.S.K., . Tetrahedron Lett. (1987), 28, 683; Padwa, A., Chiacchio, II., Dean, D.C., Schoffstall, A.M., Hassner, A., Murthy, K.S.K. Tetrahedron Lett. (1988), 29, 4169. 10. Kozikowski, A.P. Accts Chem. Res. (19841, 17, 410. 11. Satisfactory elemental analyses or HRMS were obtained for key new compounds.

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