Synthesis of a 1-benzylpiperazin-2-one nitrone and its reaction with alkynes and alkenes

Tetrahedron Letters

Volumn 37, Issue 41, 1996, Pages 7339-7342

  Bernotas, Ronald C ^a   Adams, Ginette ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ISOXAZOLIDINE DERIVATIVE; PIPERAZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030573977     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01640-1     Document Type: Article

References (23)

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2. 1. Carr, A. A.; Farr, R. A.; Kane, J. M. German patent 3 022 401, 1981; Chem. Abstr. 1981, 95 204440q. Moon, M. W. U.S. Patent 4 251 438, 1982; Chem. Abstr. 1982, 96 7084w. Takenaka, H., Miyake, H., Yasuda, M., Gemba, M., Yamashita, T., Kojima, Y. J. Chem. Soc. Perkin Trans. I 1993, 933-937.
3. 1. Carr, A. A.; Farr, R. A.; Kane, J. M. German patent 3 022 401, 1981; Chem. Abstr. 1981, 95 204440q. Moon, M. W. U.S. Patent 4 251 438, 1982; Chem. Abstr. 1982, 96 7084w. Takenaka, H., Miyake, H., Yasuda, M., Gemba, M., Yamashita, T., Kojima, Y. J. Chem. Soc. Perkin Trans. I 1993, 933-937.
4. 1. Carr, A. A.; Farr, R. A.; Kane, J. M. German patent 3 022 401, 1981; Chem. Abstr. 1981, 95 204440q. Moon, M. W. U.S. Patent 4 251 438, 1982; Chem. Abstr. 1982, 96 7084w. Takenaka, H., Miyake, H., Yasuda, M., Gemba, M., Yamashita, T., Kojima, Y. J. Chem. Soc. Perkin Trans. I 1993, 933-937.
5. 1. Carr, A. A.; Farr, R. A.; Kane, J. M. German patent 3 022 401, 1981; Chem. Abstr. 1981, 95 204440q. Moon, M. W. U.S. Patent 4 251 438, 1982; Chem. Abstr. 1982, 96 7084w. Takenaka, H., Miyake, H., Yasuda, M., Gemba, M., Yamashita, T., Kojima, Y. J. Chem. Soc. Perkin Trans. I 1993, 933-937.
6. 2. Aspinall, S. J. Chem. Soc. 1940, 62, 1202-1204 and Benjahad, A., Benhaddou, R., Granet, R., Kaouadji, M., Krausz, P., Pierarski, S., Thomasson, F., Bosgiraud, C., Delebassee, S. Tetrahedron Lett. 1994, 35, 9545-9548.
7. 2. Aspinall, S. J. Chem. Soc. 1940, 62, 1202-1204 and Benjahad, A., Benhaddou, R., Granet, R., Kaouadji, M., Krausz, P., Pierarski, S., Thomasson, F., Bosgiraud, C., Delebassee, S. Tetrahedron Lett. 1994, 35, 9545-9548.
8. 3. See Phillips, A. P. Chem. Abstr. 1962, 57, 15128h.
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10. 5. Gnichtel, H.; Schmitt, B.; and Schunk, G. Chem. Ber. 1981, 114, 2536-2541. Two other gem-dialkyl nitrones were described.
11. 6. Ali, A.; Wazeer, M. I. M. Tetrahedron 1988, 44, 187-193.
12. 7. Murahashi, S.-I.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S. J. Org. Chem. 1990, 55, 1736-1744.
13. 3) δ 159.06, 135.51, 128.98, 128.22, 128.16, 58.75, 49.11, 42.00. EIMS: 204 (100%), 132 (85%), 91 (100%).
14. 9. Alkyne and alkene substrates were chosen to avoid the generation of diastereomers upon reduction.
15. 10. Alternatively, the reactions may be run at room temperature though this generally requires 2 or more days to approach completion.
16. 11. Freeman, J. P. Chem. Rev. 1983, 83, 241-261; Liquori, A.; Ottana, R.; Romero, G.; Sidona, G.; Uccella, N. Tetrahedron 1988, 44, 1255-1265; Padwa, A.; Wong, G. S. K. J. Org. Chem. 1986, 51, 3125-3368.
17. 11. Freeman, J. P. Chem. Rev. 1983, 83, 241-261; Liquori, A.; Ottana, R.; Romero, G.; Sidona, G.; Uccella, N. Tetrahedron 1988, 44, 1255-1265; Padwa, A.; Wong, G. S. K. J. Org. Chem. 1986, 51, 3125-3368.
18. 11. Freeman, J. P. Chem. Rev. 1983, 83, 241-261; Liquori, A.; Ottana, R.; Romero, G.; Sidona, G.; Uccella, N. Tetrahedron 1988, 44, 1255-1265; Padwa, A.; Wong, G. S. K. J. Org. Chem. 1986, 51, 3125-3368.
19. 13C NMR, CIMS, and IR) data.
20. 13. LeBel, N. A.; Balasubramanian, N. J. Am. Chem. Soc. 1989, 111, 3363-3368 (for isoxazolidines).
21. 14. Cicchi, S.; Goti, A.; Brandi, A.; Guarna, A.; De Sarlo, F. Tetrahedron Lett. 1990, 31, 3351-3354.
22. 15. The diastereoselectivity of the cycloadditon is under investigation.
23. 3 eliminated trimethylsilyl alcohol to give 2a. A similar elimination has been observed: Camiletti, C., Dhavale, D. D., Gentilucci, L., Trombini, C. J. Chem. Soc. Perkin Trans. 1993, 3157-3165.