Al-MCM-41 catalyzed three-component Strecker-type synthesis of α-aminonitriles

Tetrahedron

Volumn 66, Issue 10, 2010, Pages 1898-1901

  Iwanami, Katsuyuki ^a   Seo, Hana ^a   Choi, Jun Chul ^a   Sakakura, Toshiyasu ^a   Yasuda, Hiroyuki ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

Aminonitriles; Al MCM 41; Heterogeneous catalysis; Mesoporous materials; Three component Strecker type reaction

Indexed keywords

ACETONE; ALDEHYDE DERIVATIVE; ALPHA AMINONITRILE DERIVATIVE; ALUMINUM SILICATE; AMINE; ANILINE; BENZYLACETONE; KETONE DERIVATIVE; NITRILE; SILICON DIOXIDE; TRIMETHYLSILYL CYANIDE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG; ZEOLITE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; FIXED BED REACTOR; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STRECKER SYNTHESIS;

EID: 75849164407     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.01.001     Document Type: Article

References (49)

1. Shafran Y.M., Bakulev V.A., and Mokrushin V.S. Russ. Chem. Rev. 58 (1989) 148
2. Enders D., and Shilvock J.P. Chem. Soc. Rev. 29 (2000) 359
3. Kobayashi S., Ishitani H., and Ueno M. Synlett (1997) 115
4. De S.K., and Gibbs R.A. Synth. Commun. 35 (2005) 951
5. Paraskar S., and Sudalai A. Tetrahedron Lett. 47 (2006) 5759
6. Heydari A., Fatemi P., and Alizadesh A.-A. Tetrahedron Lett. 39 (1998) 3049
7. De S.K., and Gibbs R.A. Tetrahedron Lett. 45 (2004) 7407
8. De S.K. J. Mol. Catal. A: Chem. 225 (2005) 169
9. De S.K. Synth. Commun. 35 (2005) 653
10. Pasha M.A., Nanjundaswamy H.M., and Jayashankara V.P. Synth. Commun. 37 (2007) 4371
11. Shen Z.-L., Ji S.-J., and Loh T.-P. Tetrahedron 64 (2008) 8159
12. Majhi A., Kim S.S., and Kadam S.T. Tetrahedron 64 (2008) 5509
13. Narasimhulu M., Reddy T.S., Mahesh K.C., Reddy S.M., Reddy A.V., and Venkateswarlu Y. J. Mol. Catal. A: Chem. 264 (2007) 288
14. Royer L., De S.K., and Gibbs R.A. Tetrahedron Lett. 46 (2005) 4595
15. Das B., Ramu R., Ravikanth B., and Reddy K.R. Synthesis (2006) 1419
16. Kobayashi S., Nagayama S., and Busujima T. Tetrahedron Lett. 37 (1996) 9221
17. Yadav J.S., Reddy B.V.S., Eeshwaraiah B., and Srinivas M. Tetrahedron 60 (2004) 1767
18. Chen W.-Y., and Lu J. Synlett (2005) 2293
19. Oskooie H., Heravi M.M., Sadnia A., Jannati F., and Behbahani F.K. Monatsh. Chem. 139 (2008) 27
20. Oskooie H.A., Heravi M.M., Bakhtiari K., Zadsirjan V., and Bamoharram F.F. Synlett (2006) 1768
21. Rafiee E., Rashidzadeh S., and Azad A. J. Mol. Catal. A: Chem. 261 (2007) 49
22. Rafiee E., Rashidzadeh S., Joshaghani R., Chalabeh H., and Afza K. Synth. Commun. 38 (2008) 2741
23. Heydari A., Khaksar S., Pourayoubi M., and Mahjoub A.R. Tetrahedron Lett. 48 (2007) 4059
24. Li Z., Sun Y., Ren X., Wei P., Shi Y., and Ouyang P. Synlett (2007) 803
25. Olah G.A., Mathew T., Panja C., Smith K., and Prakash G.K.S. Catal. Lett. 114 (2007) 1
26. Yadav J.S., Reddy B.V.S., Eshwaraiah B., Srinivas M., and Vishnumurthy P. New J. Chem. 27 (2003) 462
27. Martínez R., Ramón D.J., and Yus M. Tetrahedron Lett. 46 (2005) 8471
28. Matsumoto K., Kim J.C., Hayashi N., and Jenner G. Tetrahedron Lett. 43 (2002) 9167
29. Prakash G.K.S., Mathew T., Panja C., Alconcel S., Vaghoo H., Do C., and Olah G.A. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 3703
30. Prakash G.K.S., Panja C., Do C., Mathew T., and Olah G.A. Synlett (2007) 2395
31. Khan N.H., Agrawal S., Kureshy R.I., Abdi S.H.R., Singh S., Suresh E., and Jasra R.V. Tetrahedron Lett. 49 (2008) 640
32. Corma A. Chem. Rev. 97 (1997) 2373
33. On D.T., Desplantier-Giscard D., Danumah C., and Kaliaguine S. Appl. Catal., A 253 (2003) 545
34. Taguchi A., and Schüth F. Microporous Mesoporous Mater. 77 (2005) 1
35. Corma A., and Kumar D. Stud. Surf. Sci. Catal. 117 (1998) 201
36. Jermy B.R., and Pandurangan A. J. Mol. Catal., A 256 (2006) 184
37. Robinson M.W.C., and Graham A.E. Tetrahedron Lett. 48 (2007) 4727
38. Ajaikumar S., and Pandurangan A. J. Mol. Catal., A 266 (2007) 1
39. Murata H., Ishitani H., and Iwamoto M. Tetreahedron Lett. 49 (2008) 4788
40. Iwanami K., Choi J.-C., Lu B., Sakakura T., and Yasuda H. Chem. Commun. (2008) 1002
41. Ito S., Yamaguchi H., Kubota Y., and Asami M. Tetrahedron Lett. 50 (2009) 2967
42. Iwanami K., Sakakura T., and Yasuda H. Catal. Commun. 10 (2009) 1990
43. Ito S., Yamaguchi H., Kubota Y., and Asami M. Chem. Lett. 38 (2009) 700
44. 4b In our examination, when the reaction starting from benzylacetone was performed in acetonitrile in the absence of the Al-MCM-41 catalyst, the desired product was obtained in 1% yield in 24 h.
45. Forlani L., Marianucci E., and Todesco P.E. J. Chem. Res., Synop. (1984) 126
46. Sugiura M., Hagio H., Hirabayashi R., and Kobayashi S. J. Am. Chem. Soc. 123 (2001) 12510
47. Grün M., Kurganov A.A., Schacht S., Schüth F., and Unger K.K. J. Chromatogr., A 740 (1996) 1
48. Kim J.M., Kwak J.H., Jun S., and Ryoo R. J. Phys. Chem. 99 (1995) 16742
49. Nur H., Hamid H., Endud S., Hamdan H., and Ramli Z. Mater. Chem. Phys. 96 (2006) 337