Clean synthesis in water: Uncatalysed preparation of ylidenemalononitriles

Green Chemistry

Volumn 2, Issue 3, 2000, Pages 101-103

  Bigi, Franca ^a   Conforti, Maria Lina ^a   Maggi, Raimondo ^a   Piccinno, Annalisa ^a   Sartori, Giovanni ^a  

^a Dipto Chim Organ Industriale D   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038998967     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b001246g     Document Type: Article

References (70)

1. (a) G. Jones, Organic Reactions, Wiley, New York, 1967, vol. 15, p. 204;
2. (b) L. F. Tietze and U. Beifuss, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 1.11, p. 341.
3. (a) A. J. Fatiadi, Synthesis, 1978, 165 and 241 and references cited therein;
4. (b) F. Freeman, Chem. Rev., 1980, 80, 329.
5. E. Campaigne and S. W. Schneller, Synthesis, 1976, 705.
6. (a) J. L. Soto, C. Seoane, P. Zamorano and F. J. Cuadrado, Synthesis, 1981, 529;
7. (b) S. Kambe and K. Saito, Synthesis, 1981, 531;
8. (c) N. Martìn, C. Pascual, C. Seoane and J. L. Soto, Heterocycles, 1987, 26, 2811;
9. (d) M. H. Elnagdi, R. M. Abdel-Motaleb and M. Mustafa, J. Heterocycl. Chem., 1987, 24, 1677;
10. (e) F. F. Abdel-Latif, Bull. Soc. Chim. Fr., 1990, 127, 129;
11. (f) F. F. Abdel-Latif and R. M. Shaker, Indian J. Chem., Sect. B, 1990, 29, 322;
12. (g) J. M. Quintela, C. Peinador and M. J. Moreira, Tetrahedron, 1995, 51, 5901;
13. (h) R. M. Shaker, Pharmazie, 1996, 51, 148;
14. F. F. Abdel-Latif, R. M. Shaker and N. S. Abdel-Aziz, Heterocycl. Commun., 1997, 3, 245.
15. G. R. N. Jones, Nature, 1972, 235, 257.
16. (a) A. Gazit, P. Yaish, C. Gilon and A. Levitzki, J. Med. Chem., 1989, 32, 2344;
17. (b) S. Hussoin, G. B. Fitzgerald and M. M. Wick, J. Pharm. Sci., 1991, 80, 416;
18. (c) A. Gazit, N. Osherov, I. Posner, P. Yaish, E. Poradosu, C. Gilon and A. Levitzki, J. Med. Chem., 1991, 34, 1896.
19. (a) S. Cenini, F. Porta, M. Pizzotti and G. La Monica, J. Chem. Soc., Dalton Trans., 1984, 355;
20. (b) A. Robert, S. Jaguelin and J. L. Guinamant, Tetrahedron, 1986, 42, 2275;
21. (c) P. Milart and J. Sepiol, Z. Naturforsch., Teil B, 1986, 41, 371;
22. (d) N. Martin, C. Seoane, J. Carlos and J. L. Soto, Tetrahedron, 1988, 44, 5861;
23. (e) Y. El-Ahmad, J.-D. Brion and P. Reynaud, Heterocycles, 1993, 36, 1979;
24. (f) S. A.-E. Ayoubi, F. Texier-Boullet and J. Hamelin, Synthesis, 1994, 258;
25. (g) H. Bock, W. Seitz, N. Nagel, R. Baur and J. W. Bats, Z. Naturforsch., Teil B, 1997, 52, 1125.
26. I. G. Binev, Y. I. Binev, B. A. Stamboliyska and I. N. Juchnovski, J. Mol. Struct., 1997, 435, 235.
27. (a) G. Brufola, F. Fringuelli, O. Piermatti and F. Pizzo, Heterocycles, 1996, 43, 1257;
28. (b) 1997, 45, 1715.
29. (a) P. S. Rao and R. V. Venkataratnam, Tetrahedron Lett., 1991, 32, 5821;
30. (b) D. Prajapati, J. Sandhu and S. Jagir, Chem. Lett., 1992, 1945;
31. (c) D. Prajapati and J. S. Sandhu, J. Chem. Soc., Perkin Trans. 1, 1993, 739;
32. (d) R. H. Khan, H. Rahat, R. K. Mathur and A. C. Ghosh, Synth. Commun., 1996, 26, 683.
33. R. A. Sheldon, Chem. Ind., 1997, 12.
34. (a) Q. L. Wang, Y. D. Ma and B. J. Zuo, Synth. Commun., 1997, 27, 4107;
35. (b) M. M. Heravi, M. Tajbakhsh, B. Mohajerani and M. Ghassemzadeh, Ind. J. Chem., Sect. B. Org. Chem., 1999, 38, 857.
36. (a) A. Corma and R. M. Martìn-Aranda, Appl. Catal. A: General, 1993, 105, 271;
37. (b) T. I. Reddy and R. S. Varma, Tetrahedron Lett., 1997, 38, 1721.
38. S. Ernst, T. Bongers, C. Casel and S. Munsch, Stud. Surf. Sci. Catal., 1999, 125, 367.
39. (a) F. Texier-Boullet and A. Foucaud, Tetrahedron Lett., 1982, 23, 4927;
40. (b) J. A. Cabello, J. M. Campelo, A. Garcia, D. Luna and J. M. Marinas, J. Org. Chem., 1984, 49, 5195;
41. (c) H. Moison, F. Texier-Boullet and A. Foucaud, Tetrahedron, 1987, 43, 537;
42. (d) A. Foucaud, H. Moison and F. Texier-Boullet, Mol. Cryst. Liq. Cryst., 1988, 517.
43. S. Chalais, P. Laszlo and A. Mathy, Tetrahedron Lett., 1985, 26, 4453.
44. M. L. Kantam, B. M. Choudary, C. V. Reddy, K. K. Rao and F. Figueras, Chem. Commun., 1998, 1033.
45. Y. V. S. Rao and B. M. Choudary, Synth. Commun., 1991, 21, 1163.
46. Y. V. S. Rao, D. E. De Vos and P. A. Jacobs, Angew. Chem., Int. Ed. Engl., 1997, 36, 2661.
47. (a) E. Angeletti, C. Canepa, G. Martinetti and P. Venturello, J. Chem. Soc., Perkin Trans. 1, 1989, 105;
48. (b) A. Katz and M. E. Davis, Nature, 2000, 403, 286.
49. F. Bigi, L. Chesini, R. Maggi and G. Sartori, J. Org. Chem., 1999, 64, 1033.
50. L. F. Tietze and U. Beifuss, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 1.11, p. 341.
51. (a) P. Laszlo, Acc. Chem. Res., 1986, 19, 121;
52. (b) K. R. Kloestra and H. van Bekkum, J. Chem. Soc., Chem. Commun., 1995, 1005;
53. (c) P. W. Lednor and R. de Ruiter, J. Chem. Soc., Chem. Commun., 1991, 1625.
54. F. Bigi, S. Carloni, B. Frullanti, R. Maggi and G. Sartori, Tetrahedron Lett., 1999, 40, 3465.
55. N. I. Sax, Dangerous Properties of Industrial Materials, 7 edn., N.Y., 1989.
56. For review on organic synthesis in water see: (a) R. Breslow, Acc. Chem. Res., 1991, 24, 159;
57. (b) C. J. Li, Chem. Rev., 1993, 93, 2023;
58. (c) A. Lubineau, J. Augè and J. Queneau, Synthesis, 1994, 741;
59. (d) R. Breslow, K. Groves and M. U. Mayer, Org. Lett., 1999, 1, 117.
60. W. Blokzijl, M. J. Blandamer and J. B. F. N. Engberts, J. Am. Chem. Soc., 1991, 113, 4241.
61. C. F. Bernasconi, J. L. Zitomer, J. P. Fox and K. A. Howard, J. Org. Chem., 1984, 49, 482.
62. I. Lee, C. K. Kim, B-S. Lee, C. K. Kim, H. W. Lee and I. S. Han, J. Phys. Org. Chem., 1997, 10, 908.
63. S. El-Taher, Int. J. Quantum Chem., 1997, 62, 419.
64. J. P. Richard, G. Williams and J. Gao, J. Am. Chem. Soc., 1999, 121, 715 and references cited therein.
65. 2, J = 21.7 Hz), is due to the exchange of both hydrogens.
66. K. Sung, J. Chem. Soc., Perkin Trans. 2, 1999, 1169.
67. M. Hojatti, A. J. Kresge and W.-H. Wang, J. Am. Chem. Soc., 1987, 109, 4023.
68. In a preliminary experiment we observed that the reaction time can be decreased to 1 h.
69. L. N. Kurkovskaya, N. K. Genkina and V. L. Shugol, J. Struct. Chem., 1995, 35, 638.
70. The purification from traces of the starting aldehyde, if present, was performed by crystallisation.