Guanidine hydrochloride: An active and simple catalyst for Strecker type reaction

Journal of Molecular Catalysis A: Chemical

Volumn 271, Issue 1-2, 2007, Pages 142-144

  Heydari, Akbar ^a   Arefi, Afsaneh ^a   Khaksar, Samad ^a   Shiroodi, Roohollah Kazem ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

Aminonitrile; Guanidine hydrochloride; Multicomponent reaction; Strecker reaction

Indexed keywords

ALDEHYDES; CATALYSTS; METHANOL; PHASE TRANSITIONS; REACTION KINETICS;

ALPHA;-AMINONITRILE; GUANIDINE HYDROCHLORIDE; MULTICOMPONENT REACTION; STRECKER TYPE REACTION;

CRYSTALLINE MATERIALS;

EID: 34248218040     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2007.02.046     Document Type: Article

References (35)

1. Niimi L., Serita K.-I., Hiraoka S., and Yokozawa T. Tetrahedron Lett. 41 (2000) 7075
2. Kobayashi S., Akiyama R., Kawamura M., and Ishitani H. Chem. Lett. (1977) 1039
3. Strecker D. Ann. Chem. Pharm. 72 (1850) 27
4. In: Zhu J., and Bienayme H. (Eds). Multicomponent Reactions (2005), Wiley-VCH, Weinheim
5. Ramon D.J., and Yus M. Angew. Chem. Int. Ed. 44 (2005) 1602
6. Groeger H. Chem. Rev. 103 (2003) 2795
7. Ager D.J. α-Aminonitrile can be used as an acyl anion equivalent, a masked hemiaminal functionality and precursor of hydroxylamine. In: Hase T.A. (Ed). Formyl and Acyl Anions, Umpoled Synthons (1987), Wiely, New York
8. Fukuyama T., and Nunes J.J. J. Am. Chem. Soc. 110 (1988) 5196
9. Harusawa S., Hamada Y., and Shioiri T. Tetrahedron Lett. 20 (1979) 4664
10. Mai K., and Patil G. Tetrahedron Lett. 25 (1984) 4583
11. Vachal P., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 10012
12. Nakamura S., Sato N., Sugimoto M., and Toru T. Tetrahedron: Asymmetry 15 (2004) 1513
13. Bhanu Prasad B.A., Bisai A., and Singh V.K. Tetrahedron Lett. 45 (2004) 9565
14. Harusawa S., Hamada Y., and Shioiri T. Tetrahedron Lett. 20 (1979) 4663
15. Mai K., and Patil G. Tetrahedron Lett. 25 (1984) 4583
16. Iyer M.S., Gigstad K.M., Namdev N.D., and Lipton M. J. Am. Chem. Soc. 118 (1996) 4910
17. Sigman M.S., and Jacobsen E.N. J. Am. Chem. Soc. 120 (1998) 5315
18. Kobayashi S., and Ishitani H. Chem. Rev. 99 (1999) 1069
19. Takamura M., Hamashima Y., Usuda H., Kanai M., and Shibasaki M. Angew. Chem. Int. Ed. 39 (2000) 1650
20. 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. Synthesis (1980) 861
21. Chakraborty T.K., Reddy G.V., and Hussain K.A. Tetrahedron Lett. 32 (1991) 7597
22. Leblanc J., and Gibson H.W. Tetrahedron Lett. 33 (1992) 6295
23. Heydari A., Fatemi P., and Alizadeh A.-A. Tetrahedron Lett. 39 (1998) 3049
24. Kobayashi S., Nagayama S., and Busujima T. Tetrahedron Lett. 37 (1996) 9221
25. De S.K., and Gibbs R.A. J. Mol. Catal. A: Chem. 232 (2005) 12
26. De S.K. J. Mol. Catal. A: Chem. 225 (2005) 169
27. Horenstein B.A., and Nakanishi K. J. Am. Chem. Soc. 111 (1989) 6242
28. Mulzer J., Meier A., Buschmann J., and Luger P. Synthesis (1996) 123
29. De S.K. Synth. Commun. 35 (2005) 653
30. Kobayashi S., Ishitani H., and Ueno M. Synlett (1997) 115
31. Sakurai R., Suzuki S., Hashimoto J., Baba M., Itoh O., Uchida A., Hattori T., Miyano S., and Yamaura M. Org. Lett. 6 (2004) 2244
32. De S.K., and Gibbs R.A. Tetrahedron Lett. 45 (2004) 7407
33. Yadav J.S., Reddy B.V.S., Eeshwariah B., and Srinivas M. Tetrahedron 60 (2004) 1767
34. Heydari A., Arefi A., Khaksar S., and Tajbakhsh M. Catal. Commun. 7 (2006) 982
35. Ranu B.C., Dey S.S., and Hajra A. Previously, some methods failed to produce α-aminonitriles from conjugated aldehydes. Tetrahedron 58 (2002) 2529