α-nitrocycloalkanones as a new source for the one-pot synthesis of functionalized 1,4-diketones, γ-oxoaldehydes, γ-ketoesters, and methyl ω- oxoalkanoates

Tetrahedron

Volumn 54, Issue 26, 1998, Pages 7573-7580

  Ballini, Roberto ^a   Bosica, Giovanna ^a   Gigli, Fabiola ^a  

^a Dipartimento di Scienze Chimiche   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIKETONE; ALDEHYDE DERIVATIVE; ALKANOIC ACID; CYCLOALKANE DERIVATIVE; ESTER DERIVATIVE; MAGNESIUM SULFATE; METHANOL; PERMANGANATE POTASSIUM; POTASSIUM HYDROXIDE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CONJUGATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032565902     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00391-3     Document Type: Article

References (52)

1. 1. a) Fisher, R. H.; Weitz, H. M. Synthesis 1980, 261.
2. b) Rosini, G.; Ballini, R.; Petrini, M.; Marotta, E.; Righi, P. Org. Prep. Proc. Int. 1990, 22, 707.
3. 2. a) Ballini, R.; Petrini, M. Synthetic Commun. 1986, 16, 1781.
4. b) Ballini, R.; Marcantoni, E.; Petrini, M.; Rosini, G. Synthesis 1988, 915.
5. c) Ballini, R.; Petrini, M.; Rosini, G. Tetrahedron 1990, 46, 7531.
6. d) Ballini, R.; Petrini, M.; Polzonetti, V. Synthesis 1992, 355.
7. e) Ballini, R.; Bartoli, G.; Giovannini, R.; Marcantoni, E.; Petrini, M. Tetrahedron Lett. 1993, 34, 3301.
8. f) Ballini, R.; Petrini, M.; Polimanti, O. J. Org. Chem. 1996, 61, 5652.
9. g) Ballini, R.; Bosica, G. Tetrahedron 1997, 53, 16131.
10. h) Ballini, R.; Barboni, L.; Pintucci, L. Synlett 1997, 1389.
11. 3. a) Saikia, A. K.; Hazarika, M.; Barua, N. C.; Bezbarua, M. S.; Sharma, R. P.; Ghosh, A. C. Synthesis 1996, 981.
12. b) Bezbarua, M.; Saikia, A. K.; Barua, N. C.; Kalica, D. Synthesis 1996, 1289.
13. 4. Stach, H.; Hesse, M. Tetrahedron 1988, 44, 1573.
14. 5. a) Rathore, R.; Lin, Z.; Kochi, J. K. Tetrahedron Lett. 1993, 34, 1859.
15. b) VenKart Ram Reddy, M.; Kumareswaran, R.; Vankar, Y. D. Tetrahedron Lett. 1995, 36, 7149.
16. c) Dampawan, P.; Zajac, W. W. Synthesis 1983, 545.
17. d) Ballini, R.; Sorrenti, P. Org. Prep. Int. 1984, 16, 289.
18. 6. Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; John Wiley and Sons: New York, 1989.
19. 7. Ho, T. Tactics of Organic Synthesis; John Wiley and Sons: New York, 1994.
20. 8. See for example: a) Henrick, C. A. Tetrahedron 1977, 33, 1845.
21. b) Barco, A.; Benetti, S.; Baraldi, P. G.; Simoni, D. Synthesis 1981, 199.
22. c) Rosini, G.; Ballini, R.; Petrini, M.; Sorrenti, P. Tetrahedron 1984, 40, 3809.
23. d) Bestmann, H. J.; Koschatzky, K. H.; Stransky, W.; Vostrowsky, O. Tetrahedron Lett. 1976, 353.
24. e) Roelofs, W. L.; Kochansky, J.; Cardé, R.; Arn, H.; Rauscher, S. Mitt. Schweiz. Entomot. Ges. (Bull. Soc. Entomol. Swisse) 1973, 46, 71.
25. f) Muchowski, J. M.; Venuti, M. C. J. Org. Chem. 1981, 46, 459.
26. g) Bestmann, H. J.; Vostrowsky, O.; Platz, H.; Brosche, T.; Koschatzy, K. H. Tetrahedron Lett. 1979, 497.
27. h) Ujvary, I.; Kis-Tamas, A.; Novak, L. J. Chem. Ecol. 1985, 11, 113.
28. i) Kulkani, S. M.; Mandapur, V. R.; Chadha, M. S. Indian J. Chem. Sect. B 1984, 23B, 1208.
29. j) Vig, O. P.; Sharma, M. L.; Varma, N. K.; Malik, N. Indian J. Chem. Sect. B 1981, 20B, 860.
30. k) Ando, T.; Kurotsu, Y.; Kaiyo, M.; Uchiyama, M. Agric. Biol. Chem. 1985, 49, 141.
31. m) Stowell, J. C.; King, B. T. Synthesis 1983, 278.
32. n) Ballini, R.; Petrini, M.; Polzonetti, V. Synthesis 1992, 355.
33. 9. a) Ho, T.-L. Polarity Control for Synthesis; Wiley: New York, 1991; Chapter 7.
34. b) Bean, G. P. In The Chemistry ofHeterocyclic Compounds: Pyrroles; Jones, R. A.; Wiley: New York 1990, vol. 48, part 1, Chapter 2.7, pp 206-216.
35. c) Ho, T.-L. Synthetic Commun. 1974, 4, 265.
36. d) Ellison, R. A. Synthesis 1973, 397.
37. e) Piancatelli, G.; D'Auria, M.; D'Onofrio, F. Synthesis 1994, 867.
38. f) Miyakoshi, T. Org. Prep. Proc. Int. 1989, 21, 659.
39. g) Rosini, G.; Ballini, R.; Petrini, M.; Sorrenti, P. Tetrahedron 1984, 40, 3809.
40. 10. See for example: a) Cardellach, J.; Font, J.; Ortuno, R. M. J. Hetrocyclic Chem. 1984, 21, 327.
41. b) Short, K. M.; Mjalli, M. M. A. Tetrahedron Lett. 1997, 38, 359.
42. c) Frenette, R.; Mouette, M.; Bernstein, M. A.; Young, R. N.; Verhoeven, T. R. J. Org. Chem. 1991, 56, 3083.
43. d) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509.
44. 11. See for example: a) Hooz, J.; Layton, R. B. Can. J. Chem. 1972, 50, 1105.
45. b) Pelfer, A.; Harrison, C. R.; Kirk, P. Tetrahedron Lett. 1973, 45, 4491.
46. c) Patrick, T. M. J. Org. Chem. 1952, 17, 1009.
47. d) Stork, G.; Brizzalara, A.; Landesman, H.; Szmuszkovicz, V.; Terrel, R. J. Am. Chem. Soc. 1963, 85, 207.
48. e) Bao, R.; Valverde, S.; Herradon, B. Synlett 1992, 217.
49. f) Felix, D.; Gschwend-Steen, K.; Wick, A. E.; Eschenmoser, A. Helv. Chim. Acta 1969, 52, 1030.
50. g) Parker, K. A.; Kosley, R. W. Tetrahedron Lett. 1976, 5, 341.
51. h) Fujimura, T.; Aok, S.; Nakamura, E. J. Org. Chem. 1991, 56, 2809.
52. 12. Still, W. C.; Kahan, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.