A facile and efficient one-pot synthesis of nitriles from carboxylic acids

Synlett

Volumn , Issue 13, 2005, Pages 2089-2091

  Mlinarić Majerski, Kata ^a   Margeta, Renato ^a   Veljković, Jelena ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Acetonitriles; Adamantane derivatives; Carboxylic acids; Nitriles; One pot procedure

Indexed keywords

ACETONITRILE; ALIPHATIC CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; NITRILE; SULFURIC ACID;

ARTICLE; SYNTHESIS;

EID: 23944487819     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871967     Document Type: Article

References (30)

1. (a) Friedrich, K.; Wallenfels, K. In Introduction of the Cyano Group into the Molecule; Patai, S.; Rappoport, Z., Eds.; John Wiley & Sons: New York, 1970, 67-122.
2. (b) Larock, R. C. Comprehensive Organic Transformation; VCH Publishers: New York, 1989.
3. (a) Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron 1992, 48, 2613.
4. (b) Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron Lett. 1991, 52, 3321.
5. Kim, S.; Song, H.-J. Synlett 2002, 2110.
6. Sharghi, H.; Hosseini Sarvari, M. Synthesis 2003, 243.
7. Ballini, R.; Fiorini, D.; Palmieri, A. Synlett 2003, 1841.
8. Huber, V. J.; Bartsch, R. A. Tetrahedron 1998, 54, 9281.
9. (a) Vinokurov, V. A.; Ananiev, N. P.; Gaevoj, E. G.; Kuznecova, L. A.; Morsumzade, E. M.; Karahanov, R. A. Zh. Org. Khim. 1985, 21, 1806.
10. (b) Ishihara, K.; Furuya, Y.; Yamamoto, H. Angew. Chem. Int. Ed. 2002, 41, 2983.
11. (a) 1a: Stetter, H.; Schwarz, M.; Hirschhorn, A. Chem. Ber. 1959, 92, 1629.
12. (b) 2a: Stetter, H.; Mayer, J. Chem. Ber. 1962, 95, 667.
13. (c) 3a: Stetter, H.; Wulff, C. Chem. Ber. 1960, 93, 1366.
14. (d) 4a and 5a: Bott, K. Chem. Ber. 1968, 101, 564.
15. (a) Similarly, when dicarboxamide 11 was subjected to the same reaction conditions, but the reaction time was reduced to 2 h, the mixture of 11, 12, and 4b was obtained in a 1:3:3 ratio.
16. (b) Davidson, D.; Skovronek, H. J. Am. Chem. Soc. 1958, 80, 376.
17. 4, and evaporated under reduced pressure to give the crude product, which was purified by chromatography using EtOAc-hexane as eluent.
18. 13C NMR: δ = 26.92 (d), 35.56 (t), 39.75 (t), 125.01 (s).
19. Mella, M.; Freccero, M.; Soldi, T.; Fasani, E.; Albini, A. J. Org. Chem. 1996, 61, 1413.
20. Bridson, J. N.; Schriver, M. J.; Zhu, S. Can. J. Chem. 1995, 73, 212.
21. 13C NMR: δ = 28.14 (d), 31.98 (s), 32.12 (t), 36.14 (t), 41.62 (t), 117.74 (s).
22. Lauria, F.; Vecchietti, V.; Bergamaschi, M. Farmaco Ed. Sci. 1967, 22, 681.
23. 13C NMR: δ = 28.17 (d), 31.44 (t), 32.74 (s), 34.78 (t), 40.40 (t), 45.58 (t), 117.09 (s);
24. (b) For IR data of 5b see: Aigami, K.; Inamoto, Y.; Takaishi, N.; Hattori, K. J. Med. Chem. 1975, 78, 713.
25. Wender, P. A.; Eissenstat, M. A.; Sapuppo, N.; Ziegler, F. E. Org. Synth., Coll. Vol. 6 1988, 334-337.
26. Taber, D. F.; Kong, S. J. Org. Chem. 1997, 62, 8575.
27. 2: C, 70.56; H, 8.65; N, 6.33. Found: C, 70.83; H, 8.63; N, 6.46.
28. 10: Stetter, H.; Mayer, J.; Schwarz, M.; Wulff, K. Chem. Ber. 1960, 93, 226.
29. 2: C, 71.46; H, 8.99; N, 5.95. Found: C, 71.84; H, 8.88; N, 6.04.
30. 12: Anderson, G. L. US 6,348,625 B1, 2002.