An efficient and improved method for the preparation of nitriles from primary amides and aldoximes

Advanced Synthesis and Catalysis

Volumn 346, Issue 11, 2004, Pages 1271-1274

  Venkat Narsaiah, A ^a   Nagaiah, K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aldoximes; Dehydration; Nitriles; Pivaloyl chloride pyridine reagent; Primary amides

Indexed keywords

ALDOXIME; ALIPHATIC COMPOUND; AMIDE; AROMATIC COMPOUND; DICHLOROMETHANE; HETEROCYCLIC COMPOUND; NITRILE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 7044254978     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404059     Document Type: Article

References (41)

1. a) M. Chichiro, H. Nagamoto, I. Takemura, K. Kitano, H. Komatsu, K. Sekiguchi, F. Tbusa, T. Mori, M. Tomonaga, Y. Yabuuchi, J. Med. Chem. 1995, 38, 353;
2. b) J. L. Serrano, T. Sierra, Y. Gonzalez, C. Bolm, K. Weickharalt, A. Magnus, G. Moll, J. Am. Chem. Soc. 1995, 117, 8321;
3. c) B. D. Judkins, D. G. Allen, T. A. Cook, G. B. Evans, T. E. Sardharwala, Synth. Commun. 1996, 26, 4351;
4. d) S. R. Sandler, W. Karo, in: Organic Functional Group Preparations, San Diego: Academic Press. Inc., 1983, Chapter 17.
5. a) K. Friedrich, K. Wallenfels, in: The Chemistry of the Cyano Group, (Ed.: Z. Rappoport), Wiley-Interscience, New York, 1970;
6. b) D. T. Mowry, Chem. Rev. 1948, 48, 250.
7. a) D. S. Bose, A. V. Narsaiah, Tetrahedron Lett. 1998, 39, 6533;
8. b) A. K. Chakraborti, G. Kaur, Tetrahedron 1999, 55, 13265;
9. c) H. M. S. Kumar, B. V. S. Reddy, P. T. Reddy, J. S. Yadav, Synthesis 1999, 586;
10. d) I. R. Baxendale, S. V. Ley, H. F. Sneddon, Synlett 2002,775;
11. e) H. Sharghi, M. H. Sarvari, Tetrahedron 2002, 58, 10323;
12. f) F. E Chen, G. Meng, Y. Cheng, Y. Xiang, Lu, Synthesis 2000, 1519;
13. g) C. Patrice, L. Andre, M. Michael, Synthesis 1989, 451.
14. a) H. M. Meshram, Synthesis 1992, 943;
15. b) A. R. Katritzky, G. F. Zhang, W. Q. Fan, Org. Prep. Proc. Int. 1993, 25, 315;
16. c) M. Boruah, D. Konwar, J. Org. Chem. 2002, 67, 7138;
17. D. L. Luca, G. Giacomelli, A. Porcheddu, J. Org. Chem. 2002, 67, 6272;
18. e) K. Iashihara, Y. Furuya, H. Yamamoto, Angew. Chem. Int. Ed. 2002, 41, 2983;
19. f) M. P. Heck, A. Wagner, C. Mioskowski, J. Org. Chem. 1996, 61, 6486.
20. g) M. Ghiaci, K. Bakhtiari, Synth. Commun. 2001, 31, 1803.
21. a) D. S. Bose, A. V. Narsaiah, Synthesis 2001, 373;
22. b) D. S. Bose, P. R. Goud, Tetrahedron Lett. 1999, 40, 747;
23. c) J. Correia, Synthesis 1994, 1127;
24. d) C. R. Stephens, E. J. Bianco, F. J. Pilgrim, J. Am. Chem. Soc. 1955, 77, 1701;
25. e) G. E. Ficken, H. France, R. P. Linstead, J. Chem. Soc. 1954, 3730;
26. f) T. M. Bagar, C. M. Riley, Synth. Commun. 1980, 10, 479;
27. g) S. Akbar, Synthesis 1985, 184;
28. h) F. Campagna, A. Carotti, G. Casini, Tetrahedron Lett. 1977, #18#1813;
29. i) W. D. Ernest, J. H. Nicholas, J. Org. Chem. 1995, 60, 5303;
30. j) K. Iashihara, Y. Furuya, H. Yamamoto, Angew. Chem. Int. Ed. 2002, 41, 29 83;
31. k) D. S. Bose, B. Jayalaxmi, J. Org. Chem. 1999, 64, 1713.
32. S. Gao, D. Herzing, B. Wang, Synthesis 2001, 544.
33. A. J. Fatiadi, in: The Chemistry of Triple-Bonded Functional Groups, Part 2, (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1983, p. 1057.
34. G. Sosnovsky, T. A. Krogh, S. G. Umhoefer, Synthesis 1979, 722.
35. G. A. Olah, T. Keumi, Synthesis 1979, 112.
36. a) N. Kato, H. Kataoka, S. Ohbuchi, S. Tanaka H. Takeshita, J. Chem. Soc. Chem. Commun. 1988, 354;
37. b) J. M. Jacquelin, F. Marsais, A. Godard, G. B. Queguiner, Synthesis 1986, 670.
38. a) J. S. Yadav, B. V. S. Reddy, A. K. Basak, A. V. Narsaiah, Tetrahedron Lett. 2003, 44, 1047;
39. b) J. S. Yadav, B. V. S. Reddy, A. K. Basak, A. V. Narsaiah, Tetrahedron Lett. 2003, 44, 2217;
40. c) J. S. Yadav, B. V. S. Reddy, A. K. Basak, A. V. Narsaiah, Green Chem. 2003, 5;
41. d) K. Nagaiah, A. V. Narsaiah, Synthesis 2003, 1881.