Stereoselective synthesis of N,N-diaryl-2,5-dioxopiperazines from homochiral or racemic 2-bromopropananilides

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1252-1255

  D'Angeli, Ferruccio ^a   Marchetti, Paolo ^a   Rondanin, Riccardo ^a   Bertolasi, Valerio ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 PIPERAZINEDIONE DERIVATIVE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029928809     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9511051     Document Type: Article

References (47)

1. Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon Press: New York, 1979; Vol. 5, pp 259-287. Edgar, M. T.; Pettit, G. R.; Krupa, T. S. J. Org Chem. 1979, 44, 396-400. Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis; Wiley-Interscience: New York, 1987.
2. Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon Press: New York, 1979; Vol. 5, pp 259-287. Edgar, M. T.; Pettit, G. R.; Krupa, T. S. J. Org Chem. 1979, 44, 396-400. Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis; Wiley-Interscience: New York, 1987.
3. Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon Press: New York, 1979; Vol. 5, pp 259-287. Edgar, M. T.; Pettit, G. R.; Krupa, T. S. J. Org Chem. 1979, 44, 396-400. Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis; Wiley-Interscience: New York, 1987.
4. Greenstein, J. P.; Winitz M. Chemistry of the Amino Acids; John Wiley: New York, 1961; Vol. 2, pp 793-802. Nitecki, D. E.; Halpern, B.; Westley, J. W. J. Org Chem. 1968, 33, 864-866. Basiuk, V. A.; Gromovoy, T. Y.; Chuiko, A., A.; Soloshonok, V. A.; Kukhar, V. P. Synthesis 1992, 449-451. Kolar, P.; Tisler, M. J. Heterocycl. Chem. 1993, 30, 1253-1260.
5. Greenstein, J. P.; Winitz M. Chemistry of the Amino Acids; John Wiley: New York, 1961; Vol. 2, pp 793-802. Nitecki, D. E.; Halpern, B.; Westley, J. W. J. Org Chem. 1968, 33, 864-866. Basiuk, V. A.; Gromovoy, T. Y.; Chuiko, A., A.; Soloshonok, V. A.; Kukhar, V. P. Synthesis 1992, 449-451. Kolar, P.; Tisler, M. J. Heterocycl. Chem. 1993, 30, 1253-1260.
6. Greenstein, J. P.; Winitz M. Chemistry of the Amino Acids; John Wiley: New York, 1961; Vol. 2, pp 793-802. Nitecki, D. E.; Halpern, B.; Westley, J. W. J. Org Chem. 1968, 33, 864-866. Basiuk, V. A.; Gromovoy, T. Y.; Chuiko, A., A.; Soloshonok, V. A.; Kukhar, V. P. Synthesis 1992, 449-451. Kolar, P.; Tisler, M. J. Heterocycl. Chem. 1993, 30, 1253-1260.
7. Greenstein, J. P.; Winitz M. Chemistry of the Amino Acids; John Wiley: New York, 1961; Vol. 2, pp 793-802. Nitecki, D. E.; Halpern, B.; Westley, J. W. J. Org Chem. 1968, 33, 864-866. Basiuk, V. A.; Gromovoy, T. Y.; Chuiko, A., A.; Soloshonok, V. A.; Kukhar, V. P. Synthesis 1992, 449-451. Kolar, P.; Tisler, M. J. Heterocycl. Chem. 1993, 30, 1253-1260.
8. Goldberg, J.; Stein, Z.; Lin, L. W.; Hart, H. Acta Crystallogr. 1985, C41, 1539. Fischer, P. M.; Solbakken, M.; Undheim, K. Tetrahedron 1994, 50, 2277-2288
9. Goldberg, J.; Stein, Z.; Lin, L. W.; Hart, H. Acta Crystallogr. 1985, C41, 1539. Fischer, P. M.; Solbakken, M.; Undheim, K. Tetrahedron 1994, 50, 2277-2288
10. Jacobson, R. A. J. Am. Chem. Soc 1946, 68, 2628.
11. Burger, K.; Schierlinger, C.; Hollweck, W.; Mütze, K. Liebigs Ann. Chem. 1944, 399-406.
12. Nagaraj, R.; Balaram, P. Heterocycles 1977, 7, 885.
13. Sewald, N.; Seymour, L. C.; Burger, K.; Osipov, S. N.; Kolomiets, A. F.; Fokin, A. V. Tetrahedron: Asymmetry 1994, 5, 1051-1060.
14. (a) Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res., Synop. 1993, 318-319; J. Chem Res., Miniprint 1993, 2125. Porzi, G.; Sandri, S. Tetrahedron: Asymmetry 1994, 5, 453-464.
15. (a) Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res., Synop. 1993, 318-319; J. Chem Res., Miniprint 1993, 2125. Porzi, G.; Sandri, S. Tetrahedron: Asymmetry 1994, 5, 453-464.
16. (a) Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res., Synop. 1993, 318-319; J. Chem Res., Miniprint 1993, 2125. Porzi, G.; Sandri, S. Tetrahedron: Asymmetry 1994, 5, 453-464.
17. (b) Groth, U.; Hunt, H.; Forsch, B.; Schmeck, C.; Schöllkopf, U. Liebigs Ann. Chem. 1993, 715-719.
18. Oku, J.; Inoue, S. J. Chem. Soc., Chem. Commun. 1981, 229-230. Apperley, D.; North, M.; Stokoe, R. B. Tetrahedron: Asymmetry 1995, 6, 1869-1872. North, M. Synlett 1993, 807-820. Falorni, M.; Satta, M ; Conti, S.; Giacomelli, G. Tetrahedron: Asymmetry 1993, 4, 2389-2398. Lipton, M. A. Chem. Eng. News 209th ACS National Meeting, April 1995, pp 37-40.
19. Oku, J.; Inoue, S. J. Chem. Soc., Chem. Commun. 1981, 229-230. Apperley, D.; North, M.; Stokoe, R. B. Tetrahedron: Asymmetry 1995, 6, 1869-1872. North, M. Synlett 1993, 807-820. Falorni, M.; Satta, M ; Conti, S.; Giacomelli, G. Tetrahedron: Asymmetry 1993, 4, 2389-2398. Lipton, M. A. Chem. Eng. News 209th ACS National Meeting, April 1995, pp 37-40.
20. Oku, J.; Inoue, S. J. Chem. Soc., Chem. Commun. 1981, 229-230. Apperley, D.; North, M.; Stokoe, R. B. Tetrahedron: Asymmetry 1995, 6, 1869-1872. North, M. Synlett 1993, 807-820. Falorni, M.; Satta, M ; Conti, S.; Giacomelli, G. Tetrahedron: Asymmetry 1993, 4, 2389-2398. Lipton, M. A. Chem. Eng. News 209th ACS National Meeting, April 1995, pp 37-40.
21. Oku, J.; Inoue, S. J. Chem. Soc., Chem. Commun. 1981, 229-230. Apperley, D.; North, M.; Stokoe, R. B. Tetrahedron: Asymmetry 1995, 6, 1869-1872. North, M. Synlett 1993, 807-820. Falorni, M.; Satta, M ; Conti, S.; Giacomelli, G. Tetrahedron: Asymmetry 1993, 4, 2389-2398. Lipton, M. A. Chem. Eng. News 209th ACS National Meeting, April 1995, pp 37-40.
22. Oku, J.; Inoue, S. J. Chem. Soc., Chem. Commun. 1981, 229-230. Apperley, D.; North, M.; Stokoe, R. B. Tetrahedron: Asymmetry 1995, 6, 1869-1872. North, M. Synlett 1993, 807-820. Falorni, M.; Satta, M ; Conti, S.; Giacomelli, G. Tetrahedron: Asymmetry 1993, 4, 2389-2398. Lipton, M. A. Chem. Eng. News 209th ACS National Meeting, April 1995, pp 37-40.
23. Basu, G.; Kubasik, M.; Anglos, D.; Kuki, A, J. Phys. Chem. 1993, 97, 3956-3967. Anglos, D.; Bindra, V.; Kuki, A. J. Chem. Soc., Chem. Commun. 1994, 213-215.
24. Basu, G.; Kubasik, M.; Anglos, D.; Kuki, A, J. Phys. Chem. 1993, 97, 3956-3967. Anglos, D.; Bindra, V.; Kuki, A. J. Chem. Soc., Chem. Commun. 1994, 213-215.
25. Egusa, S.; Takagi, J.; Sisido, M; Imanishi, Y. Bull. Chem. Soc. Jpn. 1986, 59, 2195-2201.
26. Jeong, K.-S.; Muehldorf, A. V.; Rebek, J. J. Am. Chem. Soc. 1990, 112, 6144-6145.
27. Bergeron, R. J.; Phanstiel, O.; Yao, G. W.; Milstein, S.; Weimar, W. R. J. Am. Chem. Soc. 1994, 116, 8479-8484.
28. (a) D'Angeli, F.; Marchetti, P.; Cavicchioni, G.; Maran, F.; Bertolasi, V. Tetrahedron: Asymmetry 1991, 2, 1111-1121.
29. (b) Maran, F. J. Am. Chem. Soc. 1993, 115, 6557-6563 and references therein.
30. (c) Maran, F.; Severin, M. G.; Vianello, E.; D'Angeli, F. J. Electroanal. Chem. 1993, 352, 43-50.
31. (d) D'Angeli, F.; Marchetti, P.; Bertolasi, V J. Org. Chem. 1995, 60, 4013-4016.
32. (e) D'Angeli, F.; Marchetti, P.; Cavicchioni, G.; Catelani, G.; Moftakhari Kamrani Nejad, F. Tetrahedron: Asymmetry 1991, 1, 155-158.
33. Abenius, P.W.; Widman, O. Chem. Ber. 1888, 21, 1662-1664. Abenius, P. W Ibid. 1888, 217, 1665-1668. Svetkin, Y. V.; Andreeva, A. L. Chem. Abstr. 1970, 72, 111419. Svetkin, Y. V.; Abdrakhmatov, I. B.; Petrushina, T. F. Ibid. 1972, 76, 46136. Svetkin, Y. V.; Petrushina, T. F. Ibid. 1976, 84, 7422.
34. Abenius, P.W.; Widman, O. Chem. Ber. 1888, 21, 1662-1664. Abenius, P. W Ibid. 1888, 217, 1665-1668. Svetkin, Y. V.; Andreeva, A. L. Chem. Abstr. 1970, 72, 111419. Svetkin, Y. V.; Abdrakhmatov, I. B.; Petrushina, T. F. Ibid. 1972, 76, 46136. Svetkin, Y. V.; Petrushina, T. F. Ibid. 1976, 84, 7422.
35. Abenius, P.W.; Widman, O. Chem. Ber. 1888, 21, 1662-1664. Abenius, P. W Ibid. 1888, 217, 1665-1668. Svetkin, Y. V.; Andreeva, A. L. Chem. Abstr. 1970, 72, 111419. Svetkin, Y. V.; Abdrakhmatov, I. B.; Petrushina, T. F. Ibid. 1972, 76, 46136. Svetkin, Y. V.; Petrushina, T. F. Ibid. 1976, 84, 7422.
36. Abenius, P.W.; Widman, O. Chem. Ber. 1888, 21, 1662-1664. Abenius, P. W Ibid. 1888, 217, 1665-1668. Svetkin, Y. V.; Andreeva, A. L. Chem. Abstr. 1970, 72, 111419. Svetkin, Y. V.; Abdrakhmatov, I. B.; Petrushina, T. F. Ibid. 1972, 76, 46136. Svetkin, Y. V.; Petrushina, T. F. Ibid. 1976, 84, 7422.
37. Abenius, P.W.; Widman, O. Chem. Ber. 1888, 21, 1662-1664. Abenius, P. W Ibid. 1888, 217, 1665-1668. Svetkin, Y. V.; Andreeva, A. L. Chem. Abstr. 1970, 72, 111419. Svetkin, Y. V.; Abdrakhmatov, I. B.; Petrushina, T. F. Ibid. 1972, 76, 46136. Svetkin, Y. V.; Petrushina, T. F. Ibid. 1976, 84, 7422.
38. Granacher, C.; Wolf, G.; Weidinger, A. Helv. Chim. Acta 1928, 11, 1228. Sera, A.; Itoh, K.; Yamada, H.; Aoki, R. Heterocycles 1984, 22, 713-716. Itoh, K. Bull. Chem. Soc. Jpn. 1983, 56, 1705.
39. Granacher, C.; Wolf, G.; Weidinger, A. Helv. Chim. Acta 1928, 11, 1228. Sera, A.; Itoh, K.; Yamada, H.; Aoki, R. Heterocycles 1984, 22, 713-716. Itoh, K. Bull. Chem. Soc. Jpn. 1983, 56, 1705.
40. Granacher, C.; Wolf, G.; Weidinger, A. Helv. Chim. Acta 1928, 11, 1228. Sera, A.; Itoh, K.; Yamada, H.; Aoki, R. Heterocycles 1984, 22, 713-716. Itoh, K. Bull. Chem. Soc. Jpn. 1983, 56, 1705.
41. Okawara, T.; Harada, K Bull. Chem. Soc. Jpn. 1973, 46, 1869-1872.
42. Cavicchioni, G.; Scrimin, P.; Veronese, A. C.; Balboni, G.; D'Angeli, F. J. Chem. Soc., Perkin Trans. 1 1982, 2969-2972.
43. Ueda, T.; Saito, M.; Kato, T.; Izumiya, N. Bull. Chem. Soc. Jpn. 1983, 56, 568-572.
44. Challis, B. C.; Challis, J. A. In The Chemistry of Amides; Zabieky, J., Ed.; Interseience Publ.: New York, 1970; pp 731-752.
45. Benedetti, E.; Marsh, R. E.; Goodman, M. J. Am. Chem. Soc. 1976, 98, 6676-6684.
46. Snatzke, G.; El-Abadelah, M. M. Chem. Ber. 1973, 106, 2072-2075.
47. The author has deposited atomic coordinates for cis-8c, cis-(R,R)-8e, and trans-(R,S)-9a with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 IEZ, UK