Ac2O/K2CO3/DMSO: An efficient and practical reagent system for the synthesis of nitriles from aldoximes

Tetrahedron Letters

Volumn 55, Issue 3, 2014, Pages 639-641

  Song, Yaoping ^a   Shen, Dongguo ^a   Zhang, Qinghua ^b   Chen, Bo ^b   Xu, Guangyu ^a  

^a HUNAN NORMAL UNIVERSITY   (China)

^b Research and Development   (China)

Author keywords

Acetic anhydride; Aldoximes; Dehydration; Nilvadipine; Nitriles; Synthesis

Indexed keywords

ACETIC ANHYDRIDE; ALDOXIME; ALKALI; DIMETHYL SULFOXIDE; NILVADIPINE; NITRILE; OXIME DERIVATIVE; POTASSIUM CARBONATE;

ANALYTIC METHOD; ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; DRUG SYNTHESIS; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 84891827068     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.11.079     Document Type: Article

References (55)

1. K. Friedrich, and K. Wallenfels Z. Rappaport, The Chemistry of the Cyano Group 1970 Wiley New York
2. F.F. Fleming, L. Yao, P.C. Ravikumar, L. Funk, and B.C. Shook J. Med. Chem. 53 2010 7902 7917
3. M. Sundermeier, A. Zapf, and M. Beller Eur. J. Inorg. Chem. 2003 3513 3526
4. D.T. Mowry Chem. Rev. 42 1948 189 283
5. A.J. Fatiadi S. Patai, Z. Rappaport, Preparation and Synthetic Applications of Cyano Compounds 1983 Wiley New York
6. J.K. Augustine, R. Kumar, A. Bombrun, and A.B. Mandal Tetrahedron Lett. 52 2011 1074 1077
7. A.V. Narsaiah, and K. Nagaiah Adv. Synth. Catal. 346 2004 1271 1274
8. K. Ishihara, Y. Furuya, and H. Yamamoto Angew. Chem. 114 2002 3109 3112
9. D.R. Zuidema, A.L. Dennison, E.Y. Park, and R.C. Mebane Synth. Commun. 38 2008 3810 3815
10. S.H. Yang, and S. Chang Org. Lett. 3 2001 4209 4211
11. A.V. Narsaiah, D. Sreenu, and K. Nagaiah Synth. Commun. 36 2006 137 140
12. H. Sharghi, and M.H. Sarvari Synthesis 2003 243 246
13. V. Rammoorty, and B. Fischer J. Org. Chem. 67 2002 711 719
14. A.R. Sardarian, Z. Shahsavari-Fard, H.R. Shahsavari, and Z. Ebrahimi Tetrahedron Lett. 48 2007 2639 2643
15. M.K. Singh, and M.K. Lakshman J. Org. Chem. 74 2009 3079 3084
16. N.D. Kokare, and D.B. Shinde Monatsh. Chem. 140 2009 185 188
17. N. Iranpoor, H. Firouzabadi, and G. Aghapour Synth. Commun. 32 2002 2535 2541
18. T.A. Khan, S. Peruncheralathan, and I.H. Junjappa Synlett 2004 2019 2021
19. N. Coskun Synth. Commun. 34 2004 1625 1630
20. C.P. Miller, and D.H. Kaufman Synlett 2000 1169 1171
21. A.S. Paraskar, H.S. Jagtap, and A. Sudalai J. Chem. Res. (S) 2000 30 31
22. M. Gucma, and W.M. Golebiewski Synthesis 2008 1997 1999
23. N. Lingaiah, and R. Narender Synth. Commun. 32 2002 2391 2394
24. S. Sahu, S. Patel, and B.K. Mishra Synth. Commun. 35 2005 3123 3126
25. K. Ishihara, Y. Furuya, and H. Yamamoto Angew. Chem., Int. Ed. 41 2002 2983 2986
26. K. Yamaguchi, H. Fujiwara, Y. Ogasawara, M. Kotani, and N. Mizuno Angew. Chem., Int. Ed. 46 2007 3922 3925
27. P. Tamilselvan, Y.B. Basavaraju, E. Sampathkumar, and R. Murugesan Catal. Commun. 10 2009 716 719
28. M. Boruah, and D. Konwar J. Org. Chem. 67 2002 7138 7139
29. A. Saini, S. Kumnar, and J.S. Sandhu Indian J. Chem. Sect B 44 2005 1427 1429
30. P. Yan, P. Batamack, K.S. Prakash, and G.A. Olah Catal. Lett. 101 2005 141 143
31. D.C. Barman, A.J. Thakur, D. Prajapati, and J.S. Sandhu Chem. Lett. 2000 1196 1197
32. B. Tamami, and A.R. Kiasat Synth. Commun. 30 2000 235 242
33. X.C. Wang, L. Li, Z.J. Quan, H.P. Gong, H.L. Ye, and X.F. Cao Chin. Chem. Lett. 20 2009 651 655
34. H.M. Meshram Synthesis 1992 943 944
35. B.P. Bandgar, V.S. Sadavarte, and K.R. Sabu Synth. Commun. 29 1999 3409 3413
36. P. Supsana, T. Liaskopoulos, P.G. Tsoungas, and G. Varvonis Synlett 2007 2671 2674
37. H.S. Kim, S.H. Kim, and J.N. Kim Tetrahedron Lett. 50 2009 1717 1719
38. M. Sridhar, M.K.K. Reddy, V.V. Sairam, J. Raveendra, K.R. Godala, C. Narsaiah, B.C. Ramanaiah, and C.S. Reddy Tetrahedron Lett. 53 2012 3421 3424
39. L.D.S. Yadav, V.P. Srivastava, and R. Patel Tetrahedron Lett. 50 2009 5532 5535
40. Á. Kiss, and Z. Hell Synth. Commun. 43 2013 1778 1786
41. R.M. Denton, J. An, P. Lindovska, and W. Lewis Tetrahedron 68 2012 2899 2905
42. S. Enthaler, M. Weidauer, and F. Schröder Tetrahedron Lett. 53 2012 882 885
43. M.N.S. Rad, S. Behrouz, and A. Nekoei Synlett 23 2012 1191 1198
44. S. Gabriel, and R. Meyer Eur. J. Inorg. Chem. 14 1881 2332 2341
45. M.F. Browne, and R.L. Shriner J. Org. Chem. 22 1957 1320
46. C.R. Hauser, and E. Jordan J. Am. Chem. Soc. 57 1935 2450 2456
47. T.M. David, and R.M. Richard J. Am. Chem. Soc. 69 1947 1831
48. H.J. Anderson Can. J. Chem. 37 1959 2053 2058
49. H.J. Anderson Can. J. Chem. 46 1968 798 800
50. S. Park, Y. Choi, H. Han, S.H. Yang, and S. Chang Chem. Commun. 2003 1936 1937
51. D.S. Hoffenberg, and C.R. Hauser J. Org. Chem. 20 1955 1496 1500
52. M. Kim, J. Lee, H.-Y. Lee, and S. Chang Adv. Synth. Catal. 351 2009 1807 1812
53. 4. The solvent was evaporated under vacuum to give the nitrile products.
54. 2OH·HCl, and 2.0 equiv of NaOAc in aqueous MeOH. The crude aldoxime after general post-treatment was directly used for the dehydration reaction without further purification.
55. Y. Natoh, M. Ichihashi, and K. Okumura Chem. Pharm. Bull. 12 1991 3189 3201