Ultrasound promoted aminolysis of epoxides in aqueous media: A rapid procedure with no pH adjustment for additive-free synthesis of β-aminoalcohols

Ultrasonics Sonochemistry

Volumn 15, Issue 5, 2008, Pages 823-827

  Abaee, M Saeed ^a   Hamidi, Vahid ^a   Mojtahedi, Mohammad M ^a  

^a CHEMISTRY AND CHEMICAL ENGINEERING RESEARCH CENTER OF IRAN   (Iran)

Author keywords

Aminolysis; Aqueous media; Ultrasound irradiation; Aminoalcohols

Indexed keywords

AMINES; CATALYSTS; IRRADIATION; RING OPENING POLYMERIZATION; STEREOSELECTIVITY; ULTRASONICS;

AMINOLYSIS; AQUEOUS MEDIA; ULTRASOUND IRRADIATION; Β-AMINOALCOHOLS;

ETHERS;

ALCOHOL DERIVATIVE; ALIPHATIC AMINE; ANILINE; AROMATIC AMINE; EPOXIDE; PIPERIDINE;

AMINOLYSIS; ARTICLE; ENVIRONMENT; IRRADIATION; LIQUID; LIQUID CULTURE; PH; PRIORITY JOURNAL; RING OPENING; STEREOCHEMISTRY; SYNTHESIS; ULTRASOUND;

EID: 41549149144     PISSN: 13504177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ultsonch.2007.12.006     Document Type: Article

References (48)

1. Constable D.J.C., Dunn P.J., Hayler J.D., Humphrey G.R., Leazer Jr. J.L., Linderman R.J., Lorenz K., Manley J., Pearlman B.A., Wells A., Zaks A., and Zhang T.Y. Green Chem. 9 (2007) 411
2. Kaupp G. Angew. Chem. Int. Ed. 33 (1994) 1452
3. Grieco P.A. Organic Synthesis in Water (1998), Blackie Academic & Professional, London, UK
4. Cornils B., and Hermann W.A. Aqueous-phase Organometallic Catalysis (1998), Wiley, VCH, Weinheim, Germany
5. Li C.J., and Chan T.H. Organic Reactions in Aqueous Media (1997), Wiley, New York
6. Herreri{dotless}as C.I., Yao X., Li Z., and Li C.J. Chem. Rev. 107 (2007) 2546
7. Li C.J. Chem. Rev. 105 (2005) 3095
8. Dallinger D., and Kappe C.O. Chem. Rev. 107 (2007) 2563
9. Rogers G.A., Parsons S.M., Anderson D.C., Nilsson L.M., Bahr B.A., Kornreich W.D., Kaufman R., Jacobs R.S., and Kirtman B. J. Med. Chem. 32 (1989) 1217
10. O'Brien P. Angew. Chem. Int. Ed. 38 (1999) 326
11. Ager D.J., Prakash I., and Schaad D.R. Chem. Rev. 96 (1996) 835
12. Deyrup J.A., and Moyer C.L. J. Org. Chem. 34 (1969) 175
13. Azizi N., and Saidi M.R. Can. J. Chem. (2005) 505
14. Kamal A., Ramu R., Azhar M.A., and Khanna G.B.R. Tetrahedron Lett. 46 (2005) 2675
15. Eshghi H., Rahimizadeh M., and Shoryabi A. J. Iran. Chem. Soc. 2 (2005) 155
16. Zhao P.-Q., Xu L.-W., and Xia C.-G. Synlett (2004) 846
17. Yarapathy V.R., Mekala S., Rao B.V., and Tammishetti S. Catal. Commun. 7 (2006) 466
18. Chakraborti A.K., Kondaskar A., and Rudrawar S. Tetrahedron 60 (2004) 9085
19. Yadav J.S., Reddy B.V.S., Basak A.K., and Narsaiah A.V. Tetrahedron Lett. 44 (2003) 1047
20. Harrak Y., and Pujol M.D. Tetrahedron Lett. 43 (2002) 819
21. Khodaei M.M., Khosropour A.R., and Ghozati K. Tetrahedron Lett. 45 (2004) 3525
22. Rafiee E., Tangestaninejad S., Habibi M.H., and Mirkhani V. Synth. Commun. 34 (2004) 3673
23. Mojtahedi M.M., Saidi M.R., and Bolourtchian M. J. Chem. Res. (1999) 128
24. Robin A., Brown F., Bahamontes-Rosa N., Wu B., Beitz E., Kun J.F.J., and Flitsch S.L. J. Med. Chem. 50 (2007) 4243
25. Das U., Crousse B., Kesavan V., Bonnet-Delpon D., and Begue J.P. J. Org. Chem. 65 (2000) 6749
26. Kamal A., Adil S.F., and Arifuddin M. Ultrason. Sonochem. 12 (2005) 429
27. Surendra K., Krishnaveni N.S., and Rao K.R. Synlett (2005) 506
28. Azizi N., and Saidi M.R. Tetrahedron 63 (2007) 888
29. Wu J., and Xia H.G. Green Chem. 7 (2005) 708
30. Ollevier T., and Lavie-Compin G. Tetrahedron Lett. 45 (2004) 49
31. Azoulay S., Manabe K., and Kobayashi S. Org. Lett. 7 (2005) 4593
32. Bonollo S., Fringuelli F., Pizzo F., and Vaccaro L. Green Chem. 8 (2006) 960
33. Azizi N., and Saidi M.R. Org. Lett. 7 (2005) 3649
34. Mason T.J. Chem. Soc. Rev. 26 (1997) 443
35. Cains P.W., Martin P.D., and Price C.J. Org. Process Res. Dev. 2 (1998) 34
36. Mojtahedi M.M., Abaee M.S., Hamidi V., and Zolfaghari A. Ultrason. Sonochem. 14 (2007) 596
37. Cravotto G., and Cintas P. Chem. Soc. Rev. 35 (2006) 180
38. Dilip R.R., Jarikote V., and Srinivasan K.V. Chem. Commun. (2002) 616
39. Gholap A.R., Venkatesan K., Daniel T., Lahoti R.J., and Srinivasan K.V. Green Chem. 5 (2003) 693
40. Cravotto G., Demetri A., Nano G.M., Palmisano G., Penoni A., and Tagliapietra S. Eur. J. Org. Chem. 22 (2003) 4438
41. Mojtahedi M.M., Abaee M.S., and Abbasi H. J. Iran. Chem. Soc. 3 (2006) 93
42. Mojtahedi M.M., Abaee M.S., and Abbasi H. Can. J. Chem. (2006) 429
43. Abaee M.S., Sharifi R., Borhani S., Heravi M.M., and Motahari H. Het. Commun. 11 (2005) 415
44. Mojtahedi M.M., Abaee M.S., Heravi M.M., and Behbahani F.K. Monatsh. für Chem. 138 (2007) 95
45. Mojtahedi M.M., Abaee M.S., Bolourtchian M., and Abbasi H. Phosphorus Sulfur Silicon 182 (2007) 905
46. Mojtahedi M.M., Abaee M.S., and Hamidi V. Catal. Commun. 8 (2007) 1671
47. Abaee M.S., Mojtahedi M.M., Abbasi H., and Fatemi E.R. Synth. Commun. 38 (2008) 282
48. For H-bonded catalyzed reactions see. Schreiner P.R. Chem. Soc. Rev. 32 (2003) 289 (and references cited therein)