Ionic-liquid-supported synthesis of amines and derivatives

Synthesis

Volumn , Issue 23, 2006, Pages 4046-4052

  Debdab, Mansour ^a   Mongin, Florence ^a   Bazureau, Jean Pierre ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

Amines; Esters; Glycine derivatives; Ionic liquids; Ugi reaction

Indexed keywords

DERIVATIVES; ESTERIFICATION; ESTERS; GRAFTING (CHEMICAL); HYDROXYLATION; IONIC STRENGTH;

GLYCINE DERIVATIVES; IONIC LIQUIDS; UGI REACTIONS;

AMINES;

1 (2 HYDROXYETHYL) 3 METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE DERIVATIVE; ACETONITRILE; ACETYL CHLORIDE; AMINE; BORIC ACID; CHLORIDE; FLUOROBORIC ACID DERIVATIVE; GLYCINE; GLYCINE DERIVATIVE; IONIC LIQUID; ISOCYANATE; METHANOL; NITROGEN; PHOSPHATE; PHTHALALDEHYDE;

ARTICLE; CHEMICAL REACTION; ESTERIFICATION; ROOM TEMPERATURE; SYNTHESIS;

EID: 33845611070     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950309     Document Type: Article

References (32)

1. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149.
2. (a) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.
3. (b) Toy, P. H.; Janda, K. D. Acc. Chem. Res. 2000, 33, 546.
4. Horvath, I. T. Acc. Chem. Res. 1998, 31, 641.
5. (a) Fraga-Dubreuil, J.; Bazureau, J. P. Tetrahedron Lett. 2001, 42, 6097.
6. (b) Fraga-Dubreuil, J.; Bazureau, J. P. Tetrahedron 2003, 59, 6121.
7. (a) Welton, T. Chem. Rev. 1999, 99, 2071.
8. (b) Holbrey, D.; Seddon, K. R. Clean Prod. Process 1999, 1, 223.
9. (c) Wasserscheid, P.; Keim, W. Angew. Chem. Int. Ed. 2000, 39, 3772.
10. (d) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
11. See for example: (a) Handy, S. T.; Okello, M. Tetrahedron Lett. 2003, 44, 8399.
12. (b) Miao, W.; Chan, T. H. Org. Lett. 2003, 5, 5003.
13. (c) Anjaiah, S.; Chandrasekhar, S.; Grée, R. Tetrahedron Lett. 2004, 45, 569.
14. (d) de Kort, M.; Tuin, A. W.; Kuiper, S.; Overkleeft, H. S.; van der Marel, G. A.; Buijsman, R. C. Tetrahedron Lett. 2004, 45, 2171.
15. (e) Miao, W.; Chan, T.-H. J. Org. Chem. 2005, 70, 3251.
16. (f) Yi, F.; Peng, Y.; Song, G. Tetrahedron Lett. 2005, 46, 3931.
17. See for example: (a) Mi, X.; Luo, S.; Cheng, J.-P. J. Org. Chem. 2005, 70, 2338.
18. (b) Song, G.; Cai, Y.; Peng, Y. J. Comb. Chem. 2005, 7, 561.
19. Concerning the reactivity of the imidazolium rings, see for example: (a) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem. Int. Ed. 2004, 43, 5130.
20. (b) Handy, S. T.; Okello, M. J. Org. Chem. 2005, 70, 1915.
21. Casaschi, A.; Grigg, R.; Sansano, J. M. Tetrahedron 2001, 57, 607.
22. Fraga-Dubreuil, J.; Famelart, M.-H.; Bazureau, J. P. Org. Process Res. Dev. 2002, 6, 374.
23. The solution was prepared by mixing equimolar amounts of acetyl chloride and methanol in ethyl acetate; see: Nudelman, A.; Bechor, Y.; Falb, E.; Fischer, B.; Wexler, B. A.; Nudelman, A. Synth. Commun. 1998, 28, 471.
24. Thermal dehydrochlorination from crystalline solids such as pyridinium salts of chlorometallates has been described; see: Adams, C. J.; Crawford, P. C.; Orpen, A. G.; Podesta, T. J.; Salt, B. Chem. Commun. 2005, 2457.
25. Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168.
26. Ugi reactions are generally performed in methanol at room temperature or 40 °C (see ref. 14).
27. For an example of a reaction between a π-deficient aza-aromatic and an isocyanide, see: Ugi, I.; Böttner, E. Liebigs Ann. Chem. 1963, 670, 74.
28. Fantauzzi, P. P.; Yager, K. M. Tetrahedron Lett. 1998, 39, 1291.
29. For a similar Ugi reaction between aliphatic amines, phthalaldehydic acid, and tert-butyl isocyanide, see: Hanusch-Kompa, C.; Ugi, I. Tetrahedron Lett. 1998, 39, 2725.
30. Fayol, A.; Housseman, C.; Sun, X.; Janvier, P.; Bienaymé, H.; Zhu, J. Synthesis 2005, 161.
31. Misaki, T.; Nagase, R.; Matsumoto, K.; Tanabe, Y. J. Am. Chem. Soc. 2005, 127, 2854.
32. Prasad, A. S. B.; Stevenson, T. M.; Citineni, J. R.; Nyzam, V.; Knochel, P. Tetrahedron 1997, 53, 7237.