Regioselective electrophilic alkylation of anilines with phenylacetylene in the presence of montmorillonite KSF

Tetrahedron

Volumn 53, Issue 10, 1997, Pages 3795-3804

  Arienti, Attilio ^a   Bigi, Franca ^a   Maggi, Raimondo ^a   Marzi, Elena ^a   Moggi, Pietro ^a   Rastelli, Massimo ^a   Sartori, Giovanni ^a   Tarantola, Fabio ^a  

^a Dipto di Chimica Organica   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0031562443     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00100-2     Document Type: Article

References (42)

1. 1. Olah, G.A. "Friedel-Crafts and Related Reactions", Interscience, New York, 1964, Vol. II, part 1.
2. 2. Ecke, G.G.; Napolitano, J.P.; Filbey, A.H.; Kolka, A.J. J. Org. Chem., 1957, 22, 639; Stroh, R.; Ebersberger, J.; Harberkand, H.; Hahn, W. Angew. Chem., 1957, 69, 124.
3. 2. Ecke, G.G.; Napolitano, J.P.; Filbey, A.H.; Kolka, A.J. J. Org. Chem., 1957, 22, 639; Stroh, R.; Ebersberger, J.; Harberkand, H.; Hahn, W. Angew. Chem., 1957, 69, 124.
4. 3. Burgoyne, W.F.; Dixon, D.D.; Casey, J.P. Chemtech, 1989, 19, 690; Chitnis, S.R.; Sharma, M.M. J. Catal., 1996, 160, 84; Burgoyne, W.F.; Dixon, D.D. Appl. Catal., 1990, 63, 117; Burgoyne, W.F.; Dixon, D.D. J. Mol. Catal., 1990, 62, 61.
5. 3. Burgoyne, W.F.; Dixon, D.D.; Casey, J.P. Chemtech, 1989, 19, 690; Chitnis, S.R.; Sharma, M.M. J. Catal., 1996, 160, 84; Burgoyne, W.F.; Dixon, D.D. Appl. Catal., 1990, 63, 117; Burgoyne, W.F.; Dixon, D.D. J. Mol. Catal., 1990, 62, 61.
6. 3. Burgoyne, W.F.; Dixon, D.D.; Casey, J.P. Chemtech, 1989, 19, 690; Chitnis, S.R.; Sharma, M.M. J. Catal., 1996, 160, 84; Burgoyne, W.F.; Dixon, D.D. Appl. Catal., 1990, 63, 117; Burgoyne, W.F.; Dixon, D.D. J. Mol. Catal., 1990, 62, 61.
7. 3. Burgoyne, W.F.; Dixon, D.D.; Casey, J.P. Chemtech, 1989, 19, 690; Chitnis, S.R.; Sharma, M.M. J. Catal., 1996, 160, 84; Burgoyne, W.F.; Dixon, D.D. Appl. Catal., 1990, 63, 117; Burgoyne, W.F.; Dixon, D.D. J. Mol. Catal., 1990, 62, 61.
8. 4. Anderson, W.K.; Lai, G. Synthesis, 1995, 1287; Takamatzu, N.; Inoue, S.; Kishi, Y. Tetrahedron Lett., 1971, 4661; Sreekumar, R.; Padmakumar, R. Tetrahedron Lett., 1996, 37, 5281.
9. 4. Anderson, W.K.; Lai, G. Synthesis, 1995, 1287; Takamatzu, N.; Inoue, S.; Kishi, Y. Tetrahedron Lett., 1971, 4661; Sreekumar, R.; Padmakumar, R. Tetrahedron Lett., 1996, 37, 5281.
10. 4. Anderson, W.K.; Lai, G. Synthesis, 1995, 1287; Takamatzu, N.; Inoue, S.; Kishi, Y. Tetrahedron Lett., 1971, 4661; Sreekumar, R.; Padmakumar, R. Tetrahedron Lett., 1996, 37, 5281.
11. 5. Barluenga, J.; Aznar, F. Synthesis, 1975, 704; ibid, 1977, 195.
12. 5. Barluenga, J.; Aznar, F. Synthesis, 1975, 704; ibid, 1977, 195.
13. 6. Sartori, G.; Bigi, F.; Sartori, G.; Bigi, F.; Pastorio, A.; Porta, C.; Arienti, A.; Maggi, R.; Moretti, N.; Gnappi, G. Tetrahedron Lett., 1995, 50, 9177; Sartori, G.; Pastorio, A.; Maggi, R.; Bigi, F. Tetrahedron, 1996, 52, 8287.
14. 6. Sartori, G.; Bigi, F.; Sartori, G.; Bigi, F.; Pastorio, A.; Porta, C.; Arienti, A.; Maggi, R.; Moretti, N.; Gnappi, G. Tetrahedron Lett., 1995, 50, 9177; Sartori, G.; Pastorio, A.; Maggi, R.; Bigi, F. Tetrahedron, 1996, 52, 8287.
15. 7. a) "Comprehensive Supramolecular Chemistry", Alberti, G.; Bein, T. Eds, Pergamon, UK, 1996, Vol. 7;
16. b) Balogh, M.; Laszlo, P. "Organic Chemistry using Clays", Springer Verlag, New York, 1993;
17. c) Meurig Thomas, J. Angew. Chem., Int. Ed. Engl., 1994, 33, 913;
18. d) Ramoa Ribeiro, F.; Alvarez, R; Henriquez, C.; Lemos, F.; Lopes, J.M.; Ribeiro, M.F. J. Mol. Catal. A: Chemical, 1995, 96, 245;
19. e) Barthomeuf, D. Catal. Rev., 1996, 38, 521. C.; Lemos, F.; Lopes, J.M.; Ribeiro, M.F. J. Mol. Catal. A: Chemical, 1995, 96, 245;
20. e) Barthomeuf, D. Catal. Rev., 1996, 38, 521. C.; Lemos, F.; Lopes, J.M.; Ribeiro, M.F. J. Mol. Catal. A: Chemical, 1995, 96, 245;
21. e) Barthomeuf, D. Catal. Rev., 1996, 38, 521.
22. 8. Bausch, C.; Helmkamp, G. J. Am. Chem. Soc., 1951, 73, 3080; Hausch, C.; Crosby, D.G.; Sadoski, M.; Leo, A.; Percival, D. J. Am. Chem. Soc., 1951, 73, 704.
23. 8. Bausch, C.; Helmkamp, G. J. Am. Chem. Soc., 1951, 73, 3080; Hausch, C.; Crosby, D.G.; Sadoski, M.; Leo, A.; Percival, D. J. Am. Chem. Soc., 1951, 73, 704.
24. 9. Walter, H. Helv. Chim. Acta, 1994, 77, 608; Guo Qiang, L.; Baine, N.H. J. Org. Chem, 1988, 53, 4218.
25. 9. Walter, H. Helv. Chim. Acta, 1994, 77, 608; Guo Qiang, L.; Baine, N.H. J. Org. Chem, 1988, 53, 4218.
26. 10. Meier, W.M.; Olson, D.H. Zeolites, 1992, 12, 592.
27. 11. Information kindly furnished by Tosoh Corp.
28. 4OH 2M up to pH about 8.2. The solid was then filtered, washed with water, dried overnight at 120°C and finally calcined in air at 700°C for 16 h.
29. 13. Chen, N.Y. in "Molecular Transport and Reaction in Zeolites: Design and Application of Shape Selective Catalysis", VCH Publishers Inc., New York, 1994; Miale, J.N.; Chen, N.Y.; Weisz, P.B. J. Catal., 1966, 6, 278.
30. 2O (1.5%). Information kindly furnished by Süd-Chemie AG.
31. 15. Arduini, A.; Bigi, F.; Casiraghi, G.; Casnati, G.; Sartori, G. Synthesis, 1981, 975.
32. 16. Habib, A.M.; El-Sheikh, M.Y.; Zaki, A.B.; Morsi, S.E. J. Incl. Phen., 1986, 4, 169; Narayanan, S.; Deshpande, K. J. Mol. Catal. A: Chemical, 1995, 104, L109.
33. 16. Habib, A.M.; El-Sheikh, M.Y.; Zaki, A.B.; Morsi, S.E. J. Incl. Phen., 1986, 4, 169; Narayanan, S.; Deshpande, K. J. Mol. Catal. A: Chemical, 1995, 104, L109.
34. 17. Davies, J.E. J. Incl. Phen., 1996, 24, 133.
35. 18. Kolka, A.J.; Napolitano, J.P.; Filbey, A.H.; Ecke, G.G. J. Org. Chem., 1957, 22, 462.
36. 19. Bannore, S.N.; Bose, J.L. Indian J. Chem., 1973, 11, 631.
37. 20. Paetzold, P.I.; Stohr, G.; Maisch, H.; Lenz, H. Chem. Ber., 1968, 101, 2881.
38. 21. Schmutz, J.; Künzle, F.; Hunziker, F.; Bürki, A. Helv. Chim. Acta, 1965, 48, 336.
39. 22. Alford, E.J.; Irving, H.; Marsh, H.S.; Schofield, K. J. Chem. Soc., 1952, 3009.
40. 23. Simpson, J.C.E.; Stephenson, O. J. Chem. Soc., 1942, 353.
41. 24. Bruce, J.M. J. Chem. Soc., 1959, 2366.
42. 25. Sato, T.; Ito, T.; Ishibashi, H.; Ikeda, M. Chem. Pharm. Bull., 1990, 38, 3331.