Reductive coupling of aldimines to vicinal diamines using Zn powder in aqueous basic media

Synlett

Volumn , Issue 8, 1998, Pages 857-858

  Dutta, Manu P ^a   Baruah, Bipul ^a   Boruah, Anima ^a   Prajapati, Dipak ^a   Sandhu, Jagir S ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002267351     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1800     Document Type: Article

References (22)

1. For a review see: Block, E. Org. Reaction, 1984, 30, 457 ;
2. Ho, T. L. Synthesis, 1979, 1.
3. Michalson, E. T.; Szmuszkovicz, J. Prog. Drug. Res., 1989, 33, 135.
4. Togni, A.; Venanzi, L. M. Angew. Chem. Int. Ed. Engl., 1994, 33, 497.
5. (a) Reetz, M. T.; Jaeger, R.; Drewlies, R.; Hubel, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 103;
6. (b) Katritzky, A. R.; Fanm, W. Q.; Fu, C. J. Org. Chem., 1990, 55, 3209 and references cited therein.
7. (a) Betschart, C.; Schmidt, B.; Seebach, D. Helv. Chim. Acta., 1988, 71, 1999;
8. (b) Enholm, E. J.; Forbes, D. C.; Holub, D. P. Synth. Commun., 1990, 20, 981.
9. Fristad, W. E.; Brandvold, T. A.; Peterson, J. R.; Thompson, S. R. J. Org. Chem., 1985, 50, 3647.
10. Jung, S. H.; Kohn, J. J. Am. Chem. Soc., 1985, 107, 2931;
11. Natsugari, H.; Whitte, R. R.; Weinreeb, S. M. J. Am. Chem. Soc., ibid. 1984, 106, 7867;
12. Jung, S. H.; Kohn, H. Tetrahedron Lett., 1984, 25, 399.
13. Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett.. 1995, 36, 9241.
14. Mangeney, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, J. Synthesis, 1988. 255;
15. Recently a low valent titanium reagent prepared in situ, leads to the formation of imidazolidines when N-methyl derivatives of 1 was used see: Periasamy, M.; Reddy, M. R.; Bhaskar Kanth, J. V. Tetrahedron Lett., 1996, 37, 4767.
16. Smith, J. G.; Ho, I. J. Org. Chem., 1972, 37, 653.
17. Magnesium and zinc powder used were of commercial grade and procured from Sisco Research Laboratories Pvt. Ltd., Bombay, India.
18. Shomo, T.; Rise, N.; Oike, H.; Yashimoto, M.; Okazaki, E. Q. Tetrahedron Lett., 1992, 33, 5559;
19. Khan, N. H.; Zubari, R. H.; Siddiqui, A. A. Synth. Commun., 1980, 363;
20. Smith, J. G.; Boettger, T. J. Synth. Commun., ibid. 1981, 61;
21. Alexakis, A.; Frutos, J. C.; Mutti, S.; Mangeney, P. J. Org. Chem., 1994, 59, 3326 and references cited therein.;
22. Alexakis, A.; Mutti, S.; Mangeney, P. J. Org. Chem., 1992, 57, 1224.