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

Alfred Hassner; Rakesh Maurya

doi:10.1016/s0040-4039(00)99674-6

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

Alfred Hassner, Rakesh Maurya

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	2289-2292
Number of pages	4
Journal	Tetrahedron Letters
Volume	30
Issue number	17
DOIs	https://doi.org/10.1016/s0040-4039(00)99674-6
State	Published - 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.

Funding

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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United States - Israel Binational Agricultural Research and Development Fund

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10.1016/s0040-4039(00)99674-6

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@article{aab76a7e75d4400596c736db70bedd32,

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

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.",

author = "Alfred Hassner and Rakesh Maurya",

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.",

year = "1989",

doi = "10.1016/s0040-4039(00)99674-6",

language = "אנגלית",

volume = "30",

pages = "2289--2292",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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T1 - A route to pyrrolizidines, indolizidines and quinolizidines via intramolecular oxime olefin cycloadditions

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N1 - 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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Y1 - 1989

N2 - 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.

AB - 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.

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

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