Synthesis of ω-nitro acids and ω-amino acids by ring cleavage of α- nitrocycloalkanones

European Journal of Organic Chemistry

Volumn , Issue 1, 1999, Pages 87-90

  Ballini, Roberto ^a   Papa, Fabrizio ^a   Abate, Corrado ^a  

^a Dipto Scienze Chimiche dell'Univ   (Italy)

Author keywords

Surfactant; Water; Nitrocycloalkanones; Nitro acids

Indexed keywords

9 OXODECANOIC ACID METHYL ESTER; ALKANONE; AMINO ACID DERIVATIVE; AMMONIA; BROMINE; METHANOL; NITRO DERIVATIVE; SURFACTANT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; MASS SPECTROMETRY; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSED PHASE LIQUID CHROMATOGRAPHY; SOLUBILITY; SYNTHESIS;

EID: 0032792034     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199901)1999:1<87::AID-EJOC87>3.0.CO;2-M     Document Type: Article

References (44)

1. [1a] R. H. Fisher, H. M. Weitz, Synthesis 1980, 261-282.
2. [1b] G. Rosini, R. Ballini, M. Petrini, E. Marotta, P. Righi, Org. Prep. Proc. Int. 1990, 22, 707-746
3. R. Ballini, M. Petrini, V. Polzonetti, Synthesis 1992, 355-357.
4. R. Ballini, E. Marcantoni, M. Petrini, G. Rosini, Synthesis 1988, 915-917.
5. R. Ballini, M. Petrini, G. Rosini, Tetrahedron 1990, 46, 7531-7538.
6. R. Ballini, G. Bartoli, R. Giovannini, E. Marcantoni, M. Petrini, Tetrahedron Lett. 1993, 34, 3301-3304.
7. R. Ballini, M. Petrini, O. Polimanti, J. Org. Chem. 1996, 61, 5652-5655.
8. A. K. Saikia, M. Hazarika, N. C. Barua, M. S. Bezbarua, R. P. Sharma, A. C. Ghosh, Synthesis 1996, 981-985.
9. R. Ballini, L. Barboni, L. Pintucci, Synlett 1997, 1389-1390.
10. R. Ballini, G. Bosica, Tetrahedron 1997, 53, 16131-16138.
11. H. Stach, M. Hesse, Tetrahedron 1988, 44, 1573-1590.
12. [11a] . Ballini, G. Bosica, Tetrahedron Lett. 1996, 37, 8027-8030.
13. [11b] R. Ballini, G. Bosica, J. Org. Chem. 1997, 62, 425-427.
14. [11c] R. Ballini, G. Bosica, Eur. J. Org. Chem. 1998, 355-357.
15. G. Rosini, R. Ballini, Synthesis 1988, 833-847.
16. R. Ballini, in Studies in Natural Products Chemistry (Ed.: Attaur-Rahman), Elsevier, Amsterdam, 1997, vol. 19, p. 117-184.
17. [14a] J. T. Sparrow, J. Org. Chem. 1976, 41, 1350-1353.
18. [14b] A. B. Tabor, Tetrahedron 1996, 52, 2229-2234.
19. See for example: [15a] A. Keiichi, Y. Mutsunori, E. Yoshiaki, Jpn. Kokai Tokkyo Koho JP 62 01,748, 1985, Unitika Ltd.; Chem. Abstr. 1987, 106, 214962.
20. [15b] E. Schmid, G. Stoeppelmann, Eur Pat. Appl. EP 409,115, 1991, A.-G. Ems-Inventa; Chem. Abstr. 1991, 114, 248054.
21. [15c] T. Sakashita, Y. Zenitani, A. Ikeda, Jpn. Kokai Tokkyo Koho JP 62,156,130,1985, Mitsui Petrochemical Industries, Ltd.; Chem. Abstr. 1987, 107, 237563.
22. [15d] T. Motoi, Y. Ido, M. Oguchi, Jpn. Kokai Tokkyo Koho JP 62,161,828, 1987, Toyobo Co. Ltd.; Chem. Abstr. 1988, 108, 38653.
23. [15e] T. Shimada, M. Tamaya, Jpn. Kokai Tokkyo Koho JP 63 43,953, 1986, Daicel Chemical Industried Ltd.; Chem. Abstr. 1988, 108, 222636.
24. [15f] B. Frimlova, J. Taticek, P. Marek, O. Hajicek, O. Marek, Czech. CS 241,391,1987; Chem. Abstr. 1988, 109, 74512.
25. [15f] B. Frimlova, J. Taticek, P. Marek, O. Hajicek, O. Marek, Czech. CS 241,391,1987; Chem. Abstr. 1988, 109, 74512.
26. [15g] Y. Isegawa, M. Watanabe, Ger. Offen. DE 3,738,876, 1988, Mitsubishi Monsanto Chemical Co.; Chem. Abstr. 1988, 109, 150929.
27. [15h] A. Okada, M. Kawasumi, M. Kohaki, M. Fujimoto, Y. Kojima, T. Kurauchi, O. Kamigaito, Ger. Offen. DE 3,808,623, 1988, Toyota Central Research and Development Laboratories, Inc.; Chem. Abstr. 1989, 110, 115982.
28. [15i] A. Okada, M. Kawasumi, M. Kohaki, M. Fujimoto, Y. Kojima, T. Kurauchi, O. Kamigaito, Ger. Offen. DE 3,808,623, 1988, Toyota Central Research and Development Laboratories, Inc.; Chem. Abstr. 1989, 110, 115982.
29. T. Ichino, E. Sakai, Y. Takei, Jpn. Kokai Tokkyo Koho JP 03 15,851, 1989, Konika Co.; Chem. Abstr. 1991, 115, 38651.
30. I. Saiki, J. Iida, J. Murata, R. Ogawa, N. Nishi, K. Sugimura, S. Tokura, I. Azuma, Cancer Res. 1989, 49, 3815-3822; Chem. Abstr. 1989, 111, 108493.
31. I. Saiki, J. Iida, J. Murata, R. Ogawa, N. Nishi, K. Sugimura, S. Tokura, I. Azuma, Cancer Res. 1989, 49, 3815-3822; Chem. Abstr. 1989, 111, 108493.
32. P. Roger, J. P. Fournier, A. Martin, J. Choay, Eur. Pat. Appl. EP 238,401, 1986, SANOFI; Chem. Abstr. 1988, 108, 21494.
33. A. Cordi, C. Gillet, J. Roba, P. Niebes, D. P. Janssesn, G. Lambelin, Belg. BE 897,566, 1982, MIDIT; Chem. Abstr. 1984, 100, 210422.
34. W. Treibs, H. Walther, K. Michaelis, H. Reinheckel, S. Hauptmann, Chem. Tech. 1956, 8, 187-188.
35. S. Takagi, K. Hayashi, Chem. Pharm. Bull. 1959, 7, 96-98.
36. W. Treibs, S. Hauptmann, Chem. Ber. 1956, 89, 117-120.
37. K.-K. Ho, D. C. O'Toole, D. M. Achan, K. T. Lim, J. B. Press, A. Leone-Bay, Synth. Commun. 1996, 26, 2641-2649.
38. S. Ram, R. E. Ehrenkaufer, Tetrahedron Lett. 1984, 25, 3415-3418.
39. C. J. Li, Chem. Rev. 1993, 93, 2023-2035.
40. S. M. Roberts, F. Scheinmann, New Synthetic Routes to Prostaglandines and Tromboxanes. Academic Press, London, 1982.
41. B. M. Trost, T. N. Salzmann, K. Hiroi, J. Am. Chem. Soc. 1976, 98, 4887-4902 and references cited therein.
42. M. Petrini, R. Ballini, E. Marcantoni, G. Rosini, Synth. Commun. 1988, 18, 847-853.
43. N. Ono, Nitro Compounds: Recent Advances in Synthesis and Reactivity (Eds.: H. Feuer, A. T. Nielsen), VCH, Weinheim, 1990.
44. W. C. Still, M. Kahan, A. Mitra, J. Org. Chem. 1978, 43, 2923-2925.