Simple and highly efficient procedure for conversion of aldoximes to nitriles using N-(p-Toluenesulfonyl) imidazole

Synthetic Communications

Volumn 40, Issue 16, 2010, Pages 2429-2440

  Rad, Mohammad Navid Soltani ^a   Khalafi Nezhad, Ali ^b   Behrouz, Somayeh ^b   Amini, Zohreh ^a   Behrouz, Marzieh ^b  

^a SHIRAZ UNIVERSITY OF TECHNOLOGY   (Iran)

^b SHIRAZ UNIVERSITY   (Iran)

Author keywords

Aldoximes; DBU; dehydration; DMF; nitriles; TsIm

Indexed keywords

1,8 DIAZABICYCLO[5.4.0]UNDEC 7 ENE; 2 [2 (1,3 DIOXOISOINDOLIN 2 YL)ETHOXY]BENZONITRILE; 2 [5 (2 METHYL 4 NITRO 1H IMIDAZOL 1 YL)PENTYLOXY]BENZONITRILE; ALDOXIME; BICYCLO COMPOUND; IMIDAZOLE DERIVATIVE; N (4 TOLUENESULFONYL)IMIDAZOLE; N,N DIMETHYLFORMAMIDE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; METHODOLOGY; MOLECULAR MECHANICS;

EID: 77955030198     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903261395     Document Type: Article

References (59)

1. (a) Rappoport, Z. In The Chemistry of the Cyano Group; Wiley-Interscience: New York, 1970;
2. (b) March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons (Asia) Ltd.: Singapore, 2005;
3. (c) Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; VCH: New York, 1999;
4. (d) Mowry, D. T. The preparation of nitriles. Chem. Rev. 1947, 42, 189-283.
5. (a) Brase, S.; Gil, C.; Knepper, K.; Zimmermann, V. Organic azides: An exploding diversity of a unique class of compounds. Angew. Chem., Int. Ed. 2005, 44, 5188-5240;
6. (b) Serrano, J. L.; Sierra, T.; Gonzalez, Y.; Bolm, C.; Weickhardt, K.; Magnus, A.; Moll, G. Improving FLC properties: Simplicity, planarity, and rigidity in new chiral oxazoline derivatives. J. Am. Chem. Soc. 1995, 117, 8312-8321;
7. (c) Diana, G. D.; Cutcliffe, D.; Volkots, D. L.; Mallamo, J. P.; Bialey, T. R.; Vescio, N.; Oglesby, R. C.; Nitz, T. J.; Wetzel, J.; Giranda, V.; Pevear, D. C.; Dutko, F. J. Antipicornavirus activity of tetrazole analogs related to disoxaril. J. Med. Chem. 1993, 36, 3240-3250.
8. (a) Soli, E. D.; Manoso, A. S.; Patterson, M. C.; Deshong, P., Favor, D. A.; Hirschmann, R.; Smith, A. B. Azide and cyanide displacement via hypervalent silicate intermediates. J. Org. Chem. 1999, 64, 3171-3177;
9. (b) Lian-Hua L., Zhen-Liang P., Xin-Hua D., Yong-Min L. An environmentally benign procedure for the synthesis of aryl and arylvinyl nitriles assisted by microwave in ionic liquid. Synlett, 2006, 2094-2098;
10. (c) Harusawa, S.; Yoneda, R.; Omori, Y.; Kurihara, T. Non-aqueous cyanation of halides using lithium cyanide. Tetrahedron Lett. 1987, 28, 4189-4190.
11. 3-mediated synthesis of nitriles from aldehydes. Tetrahedron Lett. 2005, 46, 6923-6925;
12. Das B., Ramesh C., Madhusudhan P. An improved one-pot conversion of aldehydes into nitriles under microwave irradiation using ammonium acetate. Synlett, 2000, 1599-1600;
13. (c) Srinivas K. V. N. S., Bolla Reddy E., Das B. Highly convenient and efficient one-pot conversions of aldehydes into nitriles and ketones into amides using HY-zeolite. Synlett, 2002, 625-627;
14. (d) Khezri, S. H.; Azimi, N.; Mohammed-Vali, M.; Eftekhari-Sis, B.; Hashemi, M. M.; Baniasadi, M. H.; Teimouri, F. Red mud-catalyzed one-pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride under microwave irradiation. Arkivoc 2007, 15, 162-170;
15. (e) Blatter, H. M.; Lukaszewski, H.; De Stevens, G. A new general synthesis of aromatic nitriles from aldehydes. J. Am. Chem. Soc. 1961, 83, 2203;
16. (f) Talukdar, S.; Hsu, J. L.; Chou, T. C.; Fang, J. M. Direct transformation of aldehydes to nitriles using iodine in ammonia water. Tetrahedron Lett. 2001, 42, 1103-1105;
17. Lai G., Bhamare N. K., Anderson W. K. A one-pot method for the efficient preparation of aromatic nitriles from aldehydes using ammonia magnesium sulfate and manganese dioxide. Synlett, 2001, 230-231;
18. 4 catalyst. Synlett, 1999, 1569-1570;
19. (i) Miller, M. J.; Loudon, G. M. A convenient, high-yield conversion of aldehydes to nitriles. J. Org. Chem. 1975, 40, 126-127.
20. McAllister G. D., Wilfred C. D., Taylor R. J. K. Tandem oxidation processes: The direct conversion of activated alcohols into nitriles. Synlett, 2002, 1291-1292;
21. Iida S., Togo H. Direct and facile oxidative conversion of primary secondary and tertiary amines to their corresponding nitriles. Synlett, 2006, 2633-2635;
22. (c) Iida, S.; Togo, H. Iron-catalyzed cross-coupling between alkenyl and dienyl sulfonates and functionalized aryl copper reagents. Synlett 2006, 407-410, and all references cited therein.
23. (a) Rosenmund, K. W.; Struck, E. Das am ringkohlenstoff gebundene halogen und sein ersatz durch andere substituenten, I: Mitteilung: Ersatz des halogens durch die carboxyl-gruppe. Ber. 1919, 52, 1749-1756;
24. Braun J. V., Manz G. Fluoranthen und seine derivate III: Mitteilung. Ann., 1931, 488, 111-126.
25. (a) Sandmeyer, T. Ueber die ersetzung der amidgruppe durch chlor in den aromatischen substanzen. Ber. 1884, 17, 1633-1635;
26. (b) Sandmeyer, T. Zur richtigstellung. Ber. 1890, 23, 1880-1881.
27. (a) Anand, N.; Owston, N. A.; Parker, A. J.; Slatford, P. A.; Williams, J. M. J. Ruthenium-catalysed conversion of oxime ethers into nitriles. Tetrahedron Lett. 2007, 48, 7761-7763;
28. (b) Hegarty, A. F.; Tuohey, P. J. Nitrile-forming eliminations from oxime ethers. J. Chem. Soc., Perkin Trans. 2 1980, 1313-1317.
29. Yang, S. H.; Chang, S. Highly efficient and catalytic conversion of aldoximes to nitriles. Org. Lett. 2001, 3, 4209-4211.
30. Sosnovsky, G.; Krogh, J. A. A versatile method for the conversion of aldoximes to nitriles using selenium dioxide. Synthesis 1978, 703-705.
31. Olah, G. A.; Vankar, Y. D. Synthetic methods and reactions, 52: Preparation of nitriles from aldoximes via dehydration with trimethylamine= sulfur dioxide complex. Synthesis 1978, 702-703.
32. Kim, J. N.; Chung, K. H.; Ryu, E. K. Improved dehydration method of aldoximes to nitriles: Use of acetonitrile to triphenylphosphine=carbon tetrachloride system. Synth. Commun. 1990, 20, 2785-2788.
33. Foley, H. G.; Dalton, D. R. Neutral conversion of aldoximes into nitriles at low temperature. J. Chem. Soc., Chem. Commun. 1973, 628-629.
34. Gabriel, S.; Meyer, R. Ueber einige aus der dinitrophenylessigsaure darstellbare verbindungen. Ber. 1881, 14, 2332-2341.
35. Dulcere, J.-P. Vilsmeier reagent for a high yield conversion of aldoximes to nitriles. Tetrahedron Lett. 1981, 22, 1599-1600.
36. Miller, C. P.; Kaufman, D. H. Mild and efficient dehydration of oximes to nitriles mediated by the Burgess reagent. Synlett 2000, 1169-1171.
37. Chakrabarti, J. K.; Hotten, T. M. A new route to nitriles: Dehydration of aldoximes using 2,4,6-trichloro-s-triazine (cyanuric chloride). J. Chem. Soc, Chem. Commun. 1972, 1226-1227.
38. 3COCl: A new and highly efficient catalyst for dehydration of aldoximes into nitriles under solvent-free condition. Synthesis 2005, 787-790.
39. Hart-Davis, J.; Battioni, P.; Boucher, J.-L.; Mansuy, D. New catalytic properties of iron porphyrins: Model systems for cytochrome P450-catalyzed dehydration of aldoximes. J. Am. Chem. Soc. 1998, 120, 12524-12530.
40. Kim, S.; Yi, K. Y. Di-2-pyridyl sulfite: A new useful reagent for the preparation of N-sulfinylamines, nitriles, isocyanides, and carbodiimides under mild conditions. Tetrahedron Lett. 1986, 27, 1925-1928.
41. Lee, K.; Han, S. B.; Yoo, E. M.; Chung, S. R.; Oh, H.; Hong, S. Efficient transformation of aldoximes to nitriles using 2-chloro-1-methylpyridinium iodide under mild conditions. Synth. Commun. 2004, 34, 1775-1782.
42. Konwar, D.; Boruah, R. C; Sandhu, J. S. A facile dehydration and Beckmann rearrangement of oximes with aluminium iodide. Tetrahedron Lett. 1990, 31, 1063-1064.
43. 3(OTf). Synth. Commun. 1999, 29, 2747-2752.
44. Arrieta, A.; Palomo, C. Reagents and synthetic methods, 22: 1-Chlorosulfinyl-4-dimethylaminopyridinium chloride as a new reagent for the dehydration of aldoximes to nitriles. Synthesis 1983, 472-474.
45. Olah, G. A.; Vankar, Y. D.; Garcia-Luna, A. Synthetic methods and reactions, 64: Preparation of nitriles from amides and aldoximes with chlorosulfonyl isocyanate, an effective and mild dehydrating agent. Synthesis 1979, 227-228.
46. 3CN: A new alternate system for dehydration of oximes and amides in hydrated media. J. Org. Chem. 2002, 67, 7138-7139.
47. Li, D.; Shi, F.; Guo, S.; Deng, Y. Highly efficient Beckmann rearrangement and dehydration of oximes. Tetrahedron Lett. 2005, 46, 671-674.
48. Khan, T. A.; Peruncheralathan, S.; Ila, H.; Junjappa, H. S,S-Dimethyl dithiocarbonate: A useful reagent for efficient conversion of aldoximes to nitriles. Synlett 2004, 2019-2021.
49. (a) Forster, M. O.; Judd, H. M. XXVII\The triazo-group, part XII: Derivatives of para-triazobenzaldehyde. J. Chem. Soc. 1910, 254-264;
50. (b) Bentley, T. J.; Mc Ghie, J. F.; Barton, D. H. R. The synthesis of 32-oxygenated lanostane derivatives. Tetrahedron Lett. 1965, 2497-2498.
51. (a) Soltani Rad, M. N.; Behrouz, S.; Khalafi-Nezhad, A. A simple one-pot procedure for the direct conversion of alcohols into azides using TsIm. Tetrahedron Lett. 2007, 48, 3445-3449; (Pubitemid 46574785)
52. (b) Soltani Rad, M. N.; Khalafi-Nezhad, A.; Behrouz, S.; Faghihi, M. A. A simple one-pot procedure for the direct conversion of alcohols into alkyl nitriles using TsIm. Tetrahedron Lett. 2007, 48, 6779-6784; (Pubitemid 47284241)
53. (c) Soltani Rad, M. N; Behrouz, S.; Faghihi, M. A.; Khalafi-Nezhad, A. A simple procedure for the esterification of alcohols with sodium carboxylate salts using 1-tosylimidazole (TsIm). Tetrahedron Lett. 2008, 49, 1115-1120;
54. (d) Soltani Rad, M. N; Khalafi-Nezhad, A.; Behrouz, S.; Faghihi, M. A.; Zare, A.; Parhami, A. One-pot synthesis of N-alkyl purine and pyrimidine derivatives from alcohols using TsIm: A rapid entry into carboacyclic nucleoside synthesis. Tetrahedron 2008, 64, 1778-1785.
55. Some of aldoximes used in this research were not commercially available. These aldoximes were synthesized from their corresponding aldehyde using methods described in literature. Buck, J. S.; Ide, W. S. Veratronitrile. Org. Syn. Coll. Vol.II 1943, 622-624.
56. Kokel, B.; Menichi, G.; Hubert-Habart, M. A convenient one-pot conversion of arene-and heteroarene-carboxaldehyde phenylhydrazones into nitriles via reaction with N,N-dimethyldichloromethaniminium chloride. Synthesis 1985, 201-202.
57. Karmarkar, S. N.; Kelkar, S. L.; Wadia, M. S. A simple unusual one-step conversion of aromatic aldehydes into nitriles. Synthesis 1985, 510-512.
58. Saednya, A. A mild, high-yield conversion of aldoximes into nitriles using trichloroacetyl chloride=triethylamine. Synthesis 1983, 748-749.
59. Vogel, A. I. Practical Organic Chemistry; Longmans, Green and Co.: London, 1954; chap. 2, pp. 161-176.