The Efficient Chemoselective Reduction of Azides to Primary Amines

Synlett

Volumn 1997, Issue 11, 1997, Pages 1253-1254

  Boruah, Anima ^a   Baruah, Mukulesh ^a   Prajapati, Dipak ^a   Sandhu, Jagir S ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002734624     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1015     Document Type: Article

References (21)

1. Grundmann, C.; in: Houben-Weyl, Methoden der Organischen Chemie, 4th ed., Muller, E. (ed), Vol. 10/3, Georg Thieme Verlag. Stuttgart, 1965, p. 822; Sheradsky, T., The Chemistry of the Azido Group ed. by Patai, S., Interscience Publishers, London, 1971. p-333. A recent review has updated the rich scope of azide chemistry and provided exhaustive coverage of methods for the reduction of azides to amines see: Sriven, E.; Turnbull, K., Chem. Rev., 1988, 88, 297.
2. Grundmann, C.; in: Houben-Weyl, Methoden der Organischen Chemie, 4th ed., Muller, E. (ed), Vol. 10/3, Georg Thieme Verlag. Stuttgart, 1965, p. 822; Sheradsky, T., The Chemistry of the Azido Group ed. by Patai, S., Interscience Publishers, London, 1971. p-333. A recent review has updated the rich scope of azide chemistry and provided exhaustive coverage of methods for the reduction of azides to amines see: Sriven, E.; Turnbull, K., Chem. Rev., 1988, 88, 297.
3. Grundmann, C.; in: Houben-Weyl, Methoden der Organischen Chemie, 4th ed., Muller, E. (ed), Vol. 10/3, Georg Thieme Verlag. Stuttgart, 1965, p. 822; Sheradsky, T., The Chemistry of the Azido Group ed. by Patai, S., Interscience Publishers, London, 1971. p-333. A recent review has updated the rich scope of azide chemistry and provided exhaustive coverage of methods for the reduction of azides to amines see: Sriven, E.; Turnbull, K., Chem. Rev., 1988, 88, 297.
4. Ranu, B. C.; Sarkar, A.; Chakraborty, R., J. Org. Chem., 1994, 59, 4114.
5. For most recent reports using expensive samarium or samarium iodide see: Huang, Y.; Zhang, Y.; Wang, Y., Tetrahedron Lett., 1997, 38, 1065. Salunkhe, A. M.; Brown, H. C., Tetrahedron Lett., 1995, 36, 7987. Afonso, C. A. M., Tetrahedron Lett., 1995, 36, 8857. Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M., Tetrahedron Lett., 1995, 36, 7313. Using Bakers' yeast see: Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S., Synlett, 1996, 1193.
6. For most recent reports using expensive samarium or samarium iodide see: Huang, Y.; Zhang, Y.; Wang, Y., Tetrahedron Lett., 1997, 38, 1065. Salunkhe, A. M.; Brown, H. C., Tetrahedron Lett., 1995, 36, 7987. Afonso, C. A. M., Tetrahedron Lett., 1995, 36, 8857. Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M., Tetrahedron Lett., 1995, 36, 7313. Using Bakers' yeast see: Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S., Synlett, 1996, 1193.
7. For most recent reports using expensive samarium or samarium iodide see: Huang, Y.; Zhang, Y.; Wang, Y., Tetrahedron Lett., 1997, 38, 1065. Salunkhe, A. M.; Brown, H. C., Tetrahedron Lett., 1995, 36, 7987. Afonso, C. A. M., Tetrahedron Lett., 1995, 36, 8857. Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M., Tetrahedron Lett., 1995, 36, 7313. Using Bakers' yeast see: Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S., Synlett, 1996, 1193.
8. For most recent reports using expensive samarium or samarium iodide see: Huang, Y.; Zhang, Y.; Wang, Y., Tetrahedron Lett., 1997, 38, 1065. Salunkhe, A. M.; Brown, H. C., Tetrahedron Lett., 1995, 36, 7987. Afonso, C. A. M., Tetrahedron Lett., 1995, 36, 8857. Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M., Tetrahedron Lett., 1995, 36, 7313. Using Bakers' yeast see: Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S., Synlett, 1996, 1193.
9. For most recent reports using expensive samarium or samarium iodide see: Huang, Y.; Zhang, Y.; Wang, Y., Tetrahedron Lett., 1997, 38, 1065. Salunkhe, A. M.; Brown, H. C., Tetrahedron Lett., 1995, 36, 7987. Afonso, C. A. M., Tetrahedron Lett., 1995, 36, 8857. Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M., Tetrahedron Lett., 1995, 36, 7313. Using Bakers' yeast see: Baruah, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S., Synlett, 1996, 1193.
10. Yoom, N. M.; Choi, J.; Shon, Y. S., Synth. Commun., 1993, 23, 3047.
11. Alverez, S. G.; Fisher, G. B.; Singavam B., Tetrahedron Lett., 1995, 36, 2567.
12. Smith, P. A. S.; Hall, J. H.; Kan, R O., J. Am. Chem. Soc., 1962, 84, 485. Gastiser, T.; Selve, C.; Delpucch, J. J., Tetrahedron Lett., 1983, 24, 1609.
13. Smith, P. A. S.; Hall, J. H.; Kan, R O., J. Am. Chem. Soc., 1962, 84, 485. Gastiser, T.; Selve, C.; Delpucch, J. J., Tetrahedron Lett., 1983, 24, 1609.
14. Ramesha, A. R; Bhat, S.; Chandrasekan, S., J. Org. Chem., 1995, 60, 7682.
15. Zinc powder and nickel chloride used were of commercial grade and procured from Central Drug House (Pvt.) Ltd., New Delhi - 110002.
16. 4 see: Boyer, J.H., J. Am. Chem. Soc., 1951, 73, 5865.
17. 4 see: Boyer, J.H., J. Am. Chem. Soc., 1951, 73, 5865.
18. 4 see: Boyer, J.H., J. Am. Chem. Soc., 1951, 73, 5865.
19. 4 see: Boyer, J.H., J. Am. Chem. Soc., 1951, 73, 5865.
20. 4 see: Boyer, J.H., J. Am. Chem. Soc., 1951, 73, 5865.
21. Verheyden, J. P. H.; Wagner, D.; Moffatt, J. G., J. Org. Chem., 1971, 36, 250.