Highly Convenient, One-Pot Synthesis of Nitriles from Aldehydes Using the NH2OH·HCl/NaI/MeCN System

Synlett

Volumn , Issue 12, 2003, Pages 1841-1843

  Ballini, Roberto ^a   Fiorini, Dennis ^a   Palmieri, Alessandro ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

Aldehydes; Catalysis; Hydroxylamine hydrochloride; Nitriles; Sodium iodide

Indexed keywords

ACETONITRILE; ALDEHYDE DERIVATIVE; HYDROXYLAMINE; SODIUM IODIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; SOLVENT EFFECT; SYNTHESIS;

EID: 0142123941     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41408     Document Type: Article

References (30)

1. (a) Chichiro, M.; Nagamoto, H.; Takemura, I.; Kitano, K.; Komatsu, H.; Sekiguchi, K.; Tabusa, F.; Mori, T.; Tomonnaga, M.; Yabuuchi, Y. J. Med. Chem. 1995, 38, 353.
2. (b) Serrano, J. L.; Sierra, T.; Gonzales, Y.; Bolm, C.; Weickhardt, K.; Magnus, A.; Moll, G. J. Am. Chem. Soc. 1995, 117, 8321.
3. (c) Diana, G. D.; Cutcliffe, D.; Volkots, D. L.; Mallamo, J. P.; Bailey, T. R.; Velico, N.; Oglesby, R. C.; Nitz, T. J.; Wetzel, J.; Giranda, V.; Pevear, D. C.; Dutko, F. J. J. Med. Chem. 1993, 36, 3240.
4. (d) Khanna, I. K.; Weier, R. M.; Yu, Y.; Xu, X. D.; Koszyk, F. J.; Collins, P. W.; Koboldt, C. M.; Veenhuizen, A. W.; Perkins, W. E.; Casler, J. J.; Masferrer, J. L.; Zhang, Y. Y.; Gregory, S. A.; Seibert, K.; Isakson, P. C. J. Med. Chem. 1997, 40, 1634.
5. (e) Medwid, J. B.; Paul, R.; Baker, J. S.; Brockman, J. A.; Du, M. T.; Hallet, W. A.; Hanfin, J. W.; Hardy, R. A.; Tarrant, M. E.; Torley, I. M.; Wrenn, S. J. Med. Chem. 1990, 26, 4351.
6. (f) Judkins, B. D.; Allen, D. G.; Cook, T. A.; Evans, B.; Sardharwala, T. E. Synth. Commun. 1996, 26, 4351.
7. (a) March, J. Advanced Organic Chemistry; Wiley: New York, 1992, 907.
8. (b) Corey, E. J.; Cheng, X. M. The Logic of Chemical Synthesis; Wiley: New York, 1989.
9. (c) Ho, T. L. Tactics of Synthesis; Wiley: New York, 1994.
10. (d) Cohen, M. A.; Sawden, J.; Turner, N. J. Tetrahedron Lett. 1990, 31, 7223.
11. (e) Yamada, H. Chimia 1993, 47, 69.
12. (f) Crosby, J.; Moiller, J.; Parratt, J. S.; Turner, N. J. J. Chem. Soc., Perkin Trans. 1 1994, 1679.
13. (g) Luo, F.-T.; Jeevanandam, A. Tetrahedron Lett. 1998, 39, 9455.
14. (a) Cohen, M. A.; Sawden, J.; Turner, N. J. Tetrahedron Lett. 1990, 31, 7223.
15. (b) Yamada, H. Chimia 1993, 47, 69.
16. (c) Luo, F.-T.; Jeevanandam, A. Tetrahedron Lett. 1998, 39, 9455.
17. (d) Bandgar, B. P.; Jagtap, S. R.; Ghodeshwar, S. B.; Wadgaonkar, P. P. Synth. Commun. 1995, 25, 2993.
18. (e) Miller, C. P.; Kaufman, D. H. Synlett 2000, 1169.
19. (f) Lingaiah, N.; Narender, R. Synth. Commun. 2002, 32, 2391.
20. (g) Iranpoor, N.; Firouzabadi, H.; Aghapour, G. Synth. Commun. 2002, 32, 2535.
21. (a) Wang, E.-C; Lin, G.-J. Tetrahedron Lett. 1998, 36, 4047.
22. (b) Kamal, A.; Arifuddin, M.; Rao, N. V. Synth. Commun. 1998, 28, 4507.
23. (c) Webb, K. S.; Levy, D. Tetrahedron Lett. 1995, 36, 5117.
24. (d) Ali, S. L.; Nikalje, M. D.; Dewkar, G. K.; Paraskar, A. S.; Nikale, M. D.; Sudalai, A. J. Chem. Res., Synop. 2000, 30.
25. (e) Chakraborti, A. K.; Kaur, G. Tetrahedron 1999, 55, 13265.
26. (f) Das, B.; Ramesh, C.; Madhusudham, P. Synlett 2000, 1599.
27. (g) Sharghi, H.; Sarvari, M. H. Tetrahedron 2002, 58, 10323.
28. (h) Boruah, M.; Konwar, D. J. Org. Chem. 2002, 67, 7138.
29. Srinivas, K. V. N. S.; Reddy, B. E.; Das, B. Synlett 2002, 625.
30. (j) Sharghi, H.; Sarvari, M. H. Synthesis 2003, 243.