Trifluoroethanol as a metal-free, homogeneous and recyclable medium for the efficient one-pot synthesis of α-amino nitriles and α-amino phosphonates

Tetrahedron Letters

Volumn 50, Issue 1, 2009, Pages 77-80

  Heydari, Akbar ^a   Khaksar, Samad ^a   Tajbakhsh, Mahmood ^b  

^a TARBIAT MODARES UNIVERSITY   (Iran)

^b UNIVERSITY OF MAZANDARAN   (Iran)

Author keywords

Amino nitriles; Amino phosphonates; Fluorous solvents; Hydrogen bonding; Trifluoroethanol; Trimethylsilyl cyanide

Indexed keywords

ALDEHYDE DERIVATIVE; ALPHA AMINO NITRILE DERIVATIVE; ALPHA AMINO PHOSPHONATE DERIVATIVE; AMINE; CYANIDE; KETONE DERIVATIVE; NITRILE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; TRIFLUOROETHANOL; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS;

EID: 56949083332     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.10.106     Document Type: Article

References (59)

1. Shuklov I.A., Dubrorina N.V., and Boerner A. Synthesis 19 (2007) 2925
2. Deng X.H., and Mani N.S. J. Org. Chem. 72 (2008) 2412
3. Qiao R.Z., Xu B.L., and Wang Y.H. Chin. Chem. Lett. 18 (2007) 656
4. Zmitek K., Stavber S., Zupan M., Bonnet-Delpon D., and Iskra J. Tetrahedron 62 (2006) 1479
5. Di Salvo A., David M., Crousse B., and Bonnet-Delpon D. Adv. Synth. Catal. 348 (2006) 118
6. For a review see. Begue J.P., Bonnet-Delpon D., and Crousse B. Synlett (2004) 18
7. Niimi L., Serita K.-I., Hiraoka S., and Yokozawa T. Tetrahedron Lett. 41 (2000) 7075
8. Kobayashi S., Akiyama R., Kawamura M., and Ishitani H. Chem. Lett. (1973) 1039
9. Heydari A., Khaksar S., and Tajbakhsh M. Synthesis 19 (2008) 3126
10. Weinstok L.M., Davis P., Handelsman B., and Tull R. J. Org. Chem. 32 (1967) 2832
11. Matier W.L., Owens D.A., Comer W.T., Deitchman D., Ferguson H.C., Seidehmel R.J., and Young J.R. J. Med. Chem. 16 (1973) 901
12. Strecker D. Ann. Chem. Pharm. 72 (1850) 27
13. Bhanu Prasad B.A., Bisai A., and Singh V.K. Tetrahedron Lett. 45 (2004) 9565
14. Nakamura S., Sato N., Sugimoto M., and Toru T. Tetrahedron: Asymmetry 15 (2004) 1513
15. Harusawa S., Hamada Y., and Shioiri T. Tetrahedron Lett. 20 (1979) 4663
16. Vachal P., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 10012
17. Harusawa S., Hamada Y., and Shioiri T. Tetrahedron Lett. 20 (1979) 4663
18. Mai K., and Patil G. Tetrahedron Lett. 25 (1984) 4583
19. Iyer M.S., Gigstad K.M., Namdev N.D., and Lipton M. J. Am. Chem. Soc. 118 (1996) 4910
20. Sigman M.S., and Jacobsen E.N. J. Am. Chem. Soc. 120 (1998) 5315
21. Kobayashi S., and Ishitani H. Chem. Rev. 99 (1999) 1069
22. Takamura M., Hamashima Y., Usuda H., Kanai M., and Shibasaki M. Angew. Chem., Int. Ed. 39 (2000) 1650
23. 2P(O)CN is cumbersome due to their hazardous nature, while special equipment and care are needed for transfer of these materials on large scale. Groutas W.C., and Felker D. Synthesis (1980) 861
24. Heydari A., Fatemi P., and Alizadeh A.A. Tetrahedron Lett. 39 (1998) 3049
25. Kobayashi S., Nagayama S., and Busujima T. Tetrahedron Lett. 37 (1996) 9221
26. De S.K., and Gibbs R.A. J. Mol. Catal. A: Chem. 232 (2005) 12
27. De S.K. J. Mol. Catal. A: Chem. 225 (2005) 169
28. Horenstein B.A., and Nakanishi K. J. Am. Chem. Soc. 111 (1989) 6242
29. Mulzer J., Meier A., Buschmann J., and Luger P. Synthesis (1996) 123
30. De S.K. Synth. Commun. 35 (2005) 653
31. Kobayashi S., Ishitani H., and Ueno M. Synlett (1997) 115
32. Sakurai R., Suzuki S., Hashimoto J., Baba M., Itoh O., Uchida A., Hattori T., Miyano S., and Yamaura M. Org. Lett. 6 (2004) 2244
33. De S.K., and Gibbs R.A. Tetrahedron Lett. 45 (2004) 7407
34. Yadav J.S., Reddy B.V.S., Eeshwariah B., and Srinivas M. Tetrahedron 60 (2004) 1767
35. Previously, some methods have failed to produce α-aminonitriles from conjugated aldehydes. Ranu B.C., Dey S.S., and Hajra A. Tetrahedron 58 (2002) 2529
36. Enzyme inhibitors. Allen M.C., Fuhrer W., Tuck B., Wade R., and Wood J.M. J. Med. Chem. 32 (1989) 1652
37. Antibiotics:. Atherton F.R., Hassal C.H., and Lambert R.W. J. Med. Chem. 29 (1986) 29
38. Herbicides:. Maier L. Phosphorus, Sulfur, Silicon Relat. Elem. 53 (1990) 43
39. Fungicides and plant growth regulators. Maier L., and Spoerri H. Phosphorus, Sulfur, Silicon Relat. Elem. 61 (1991) 69
40. Anti-thrombotic agents. Meyer J.H., and Barlett P.A. J. Am. Chem. Soc. 120 (1998) 4600
41. Peptidases and proteinases:. Miller D.J., Hammond S.M., Anderluzzi D., and Bugg T.D.H. J. Chem. Soc., Perkin Trans. 1 (1998) 131
42. Microreactor:. Van Meenen E., Moonen K., Acke D., and Stevens C.V. ARKIVOC (2006) 31
43. Lewis acids including lanthanide triflate. Manabe K., and Kobayashi S. Chem. Commun. (2000) 669
44. Samarium diiodide:. Xu F., Luo Y., Deng M., and Shen Q. Eur. J. Org. Chem. (2003) 4728
45. Scandium tris(dodecylsulfate):. Manabe K., and Kobayashi S. Chem. Commun. (2000) 669
46. Indium(III) chloride:. Ranu B.C., Hajra A., and Jana J. Org. Lett. 1 (1999) 1141
47. 2:. Chandrasekhar S., Jaya Prakash S., Jagadeshwar V., and Narsihmula Ch. Tetrahedron Lett. 42 (2001) 5561
48. (Bromodimethyl)sulfonium bromide:. Kudrimoti S., and Rao Bommena V. Tetrahedron Lett. 46 (2005) 1209
49. Lithium perchlorate:. Heydari A., Zarei M., Alijanianzadeh R., and Tavakol H. Tetrahedron Lett. 42 (2001) 3629
50. Alumina-supported reagents as catalysts:. Kaboudin B., and Nazari R. Tetrahedron Lett. 42 (2001) 8211 Although this approach is satisfactory for reactions with aromatic aldehydes, aminophosphonates from aliphatic aldehydes are obtained in moderate yields
51. Ionic liquid. Yadav J.S., Reddy B.V.S., and Sreedhar P. Green Chem. 4 (2002) 436
52. 3 in ionic liquid:. Lee S., Park J.H., Kang J., and Lee J.K. Chem. Commun. (2001) 1698
53. 2. Bhagat S., and Chakraborti A.K. J. Org. Chem. 72 (2007) 1263
54. 2. Xu F., Luo Y., Deng M., and Shen Q. Eur. J. Org. Chem. 4 (2003) 4728
55. Chandrasekhar S., Prakash S.J., Jagadeshwar V., and Nasihmula C. Tetrahedron Lett. 46 (2005) 1209
56. Vahdat S.M., Baharfar R., Tajbakhsh M., Heydari A., Baghbanian S.M.., and Khaksar S. Tetrahedron Lett. 49 (2008) 6501
57. Prakash G.K.S., Panja C., Do C., Mathew T., and Olah G.A. Synlett (2007) 2395
58. Heydari A., Khaksar S., Pourayoubi M., and Mahjoub A.R. Tetrahedron Lett. 48 (2007) 4059
59. Tajbakhsh M., Heydari A., Alinezhad H., Ghanei M., and Khaksar S. Synthesis (2008) 352