Reaction of aliphatic amines with acetoacetanilide in the presence of zeolite catalyst. Solvent-free synthesis of symmetric N,N'-dialkylureas

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 1004-1006

  Bigi, Franca ^a   Frullanti, Bettina ^a   Maggi, Raimondo ^a   Sartori, Giovanni ^a   Zambonin, Elena ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETANILIDE DERIVATIVE; ALIPHATIC AMINE; ALKYL GROUP; BENZYLAMINE DERIVATIVE; SOLVENT; UREA DERIVATIVE; ZEOLITE;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION TIME;

EID: 0033525110     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981109g     Document Type: Article

References (32)

1. (a) Hölderich, W. F. Organic Reactions in Zeolites. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Ed.; Pergamon: New York, 1996; Vol. 7, p 671.
2. (b) Balogh, M.; Laszlo, P. Organic Chemistry Using Clays; Springer-Verlag: New York, 1993.
3. (c) Mizuno, N.; Misono, M. Chem. Rev. 1998, 98, 199.
4. (a) Sheldon, R. A. Chem. Ind. (London) 1992, 903.
5. (b) Sheldon, R. A. J. Mol. Catal., A 1996, 107, 75.
6. (c) Dittmer, D. C. Chem. Ind. (London) 1997, 779.
7. (a) Sartori, G.; Bigi, F.; Pastorio, A.; Porta, C.; Arienti, A.; Maggi, R.; Moretti, N.; Gnappi, G. Tetrahedron Lett. 1995, 36, 9177.
8. (b) Sartori, G.; Pastorio, A.; Maggi, R.; Bigi, F. Tetrahedron 1996, 52, 8287.
9. (c) Ballini, R.; Bigi, F.; Carloni, S.; Maggi, R.; Sartori, G. Tetrahedron Lett. 1997, 38, 4169.
10. (d) Ballini, R.; Bosica, G.; Maggi, R.; Sartori, G. Synlett 1997, 795.
11. (e) Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Sartori, G. J. Org. Chem. 1997, 62, 7024.
12. Bigi, F.; Maggi, R.; Sartori, G.; Zambonin, E. J. Chem. Soc., Chem. Commun. 1998, 513.
13. Vishnyakova, T. P.; Golubeva, I. A.; Glebova, E. V. Russ. Chem. Rev. (Engl. Transl.) 1985, 54, 249.
14. (a) March, J. Advanced Organic Chemistry; John Wiley & Sons: New York, 1985; p 370.
15. (b) Knölker, H.-J.; Braxmeier, T.; Schlechtingen, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2497.
16. 3-TPD): Berteau, P.; Delmon, B. Catal. Today 1989, 5, 121.
17. Product analyses were carried out by HPLC.
18. (a) Werner, W. Tetrahedron 1969, 25, 255.
19. (b) Werner, W. Tetrahedron 1971, 27, 1755.
20. Farneth, W. E.; Gorte, R. J. Chem. Rev. 1995, 95, 615.
21. 3-TPD and FTIR pyridine absorption methods suggests that the acidity of zeolite HSZ-330 is mainly ascribable to Brönsted sites; on the contrary, Lewis sites are the most numerous in the zeolite HSZ-360.
22. 2O 0.06.
23. 2O 0.2.
24. Brandt, S.; Wolf, E. Ger. Offen. 1976, 2,640,409.
25. Srivastava, S. C.; Shurimal, A. K.; Srivastava, A. J. Organomet. Chem. 1991, 414, 65.
26. Ross, S.; Muenster, L. J. Can. J. Chem. 1961, 39, 401.
27. Scott, F. L.; Scott, M. T. J. Am. Chem. Soc. 1957, 79, 6077.
28. Grotjahn, D. B.; Joubran, C. Tetrahedron: Asymmetry 1995, 6, 745.
29. Moyer, M. I.; McEwen, W. E. J. Am. Chem. Soc. 1951, 73, 3075.
30. Kayumov, V.; Smushkevich, Y. I.; Suvorov, N. N. Khim. Geterotsikl. Soedin 1973, 6, 756.
31. Skinner, W. A.; Crawford, H. T.; Rutledge, L. C.; Moussa, M. A. J. Pharm. Sci. 1979, 68, 391.
32. Beaver, D. J.; Roman, D. P.; Stoffel, P. J. J. Am. Chem. Soc. 1957, 79, 1236.