A practical procedure for the synthesis of alkyl azides at ambient temperature in dimethyl sulfoxide in high purity and yield

Synthesis

Volumn , Issue 4, 1997, Pages 413-414

  Alvarez, Salvador G ^a   Alvarez, Miho T ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE;

ARTICLE; DRUG PURIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030996786     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1206     Document Type: Article

References (31)

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16. Brewster, P.; Hiron, F.; Hughes, E. D.; Ingold, C. K.; Rao, P. A. Nature 1950, 166, 178. Lieber, E.; Chao, T. S.; Rao, C. N. R. J. Org. Chem. 1957, 22, 238. Reeves, W. P.; Bahr, M. L. Synthesis 1976, 823. Nakajima, Y.; Kinishi, R.; Oda, J.; Inouye, Y. Bull. Chem. Soc. Jpn. 1977, 50, 2025. Jorapur, V. S.; Khalil, Z. H.; Duffley, R. P.; Razdan, R. K.; Martin, B. R.; Harris, L. S.; Dewey, W. L. J. Med. Chem. 1985, 28, 783. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. Hassner, A.; Stern M. Angew. Chem., Int. Ed. Engl. 1986, 25, 478. Koziara, A.; Zwierzak, A. Synthesis 1992, 1063. Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114.
17. Brewster, P.; Hiron, F.; Hughes, E. D.; Ingold, C. K.; Rao, P. A. Nature 1950, 166, 178. Lieber, E.; Chao, T. S.; Rao, C. N. R. J. Org. Chem. 1957, 22, 238. Reeves, W. P.; Bahr, M. L. Synthesis 1976, 823. Nakajima, Y.; Kinishi, R.; Oda, J.; Inouye, Y. Bull. Chem. Soc. Jpn. 1977, 50, 2025. Jorapur, V. S.; Khalil, Z. H.; Duffley, R. P.; Razdan, R. K.; Martin, B. R.; Harris, L. S.; Dewey, W. L. J. Med. Chem. 1985, 28, 783. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. Hassner, A.; Stern M. Angew. Chem., Int. Ed. Engl. 1986, 25, 478. Koziara, A.; Zwierzak, A. Synthesis 1992, 1063. Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114.
18. Brewster, P.; Hiron, F.; Hughes, E. D.; Ingold, C. K.; Rao, P. A. Nature 1950, 166, 178. Lieber, E.; Chao, T. S.; Rao, C. N. R. J. Org. Chem. 1957, 22, 238. Reeves, W. P.; Bahr, M. L. Synthesis 1976, 823. Nakajima, Y.; Kinishi, R.; Oda, J.; Inouye, Y. Bull. Chem. Soc. Jpn. 1977, 50, 2025. Jorapur, V. S.; Khalil, Z. H.; Duffley, R. P.; Razdan, R. K.; Martin, B. R.; Harris, L. S.; Dewey, W. L. J. Med. Chem. 1985, 28, 783. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. Hassner, A.; Stern M. Angew. Chem., Int. Ed. Engl. 1986, 25, 478. Koziara, A.; Zwierzak, A. Synthesis 1992, 1063. Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114.
19. Brewster, P.; Hiron, F.; Hughes, E. D.; Ingold, C. K.; Rao, P. A. Nature 1950, 166, 178. Lieber, E.; Chao, T. S.; Rao, C. N. R. J. Org. Chem. 1957, 22, 238. Reeves, W. P.; Bahr, M. L. Synthesis 1976, 823. Nakajima, Y.; Kinishi, R.; Oda, J.; Inouye, Y. Bull. Chem. Soc. Jpn. 1977, 50, 2025. Jorapur, V. S.; Khalil, Z. H.; Duffley, R. P.; Razdan, R. K.; Martin, B. R.; Harris, L. S.; Dewey, W. L. J. Med. Chem. 1985, 28, 783. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. Hassner, A.; Stern M. Angew. Chem., Int. Ed. Engl. 1986, 25, 478. Koziara, A.; Zwierzak, A. Synthesis 1992, 1063. Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114.
20. Brewster, P.; Hiron, F.; Hughes, E. D.; Ingold, C. K.; Rao, P. A. Nature 1950, 166, 178. Lieber, E.; Chao, T. S.; Rao, C. N. R. J. Org. Chem. 1957, 22, 238. Reeves, W. P.; Bahr, M. L. Synthesis 1976, 823. Nakajima, Y.; Kinishi, R.; Oda, J.; Inouye, Y. Bull. Chem. Soc. Jpn. 1977, 50, 2025. Jorapur, V. S.; Khalil, Z. H.; Duffley, R. P.; Razdan, R. K.; Martin, B. R.; Harris, L. S.; Dewey, W. L. J. Med. Chem. 1985, 28, 783. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. Hassner, A.; Stern M. Angew. Chem., Int. Ed. Engl. 1986, 25, 478. Koziara, A.; Zwierzak, A. Synthesis 1992, 1063. Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114.
21. Brewster, P.; Hiron, F.; Hughes, E. D.; Ingold, C. K.; Rao, P. A. Nature 1950, 166, 178. Lieber, E.; Chao, T. S.; Rao, C. N. R. J. Org. Chem. 1957, 22, 238. Reeves, W. P.; Bahr, M. L. Synthesis 1976, 823. Nakajima, Y.; Kinishi, R.; Oda, J.; Inouye, Y. Bull. Chem. Soc. Jpn. 1977, 50, 2025. Jorapur, V. S.; Khalil, Z. H.; Duffley, R. P.; Razdan, R. K.; Martin, B. R.; Harris, L. S.; Dewey, W. L. J. Med. Chem. 1985, 28, 783. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. Hassner, A.; Stern M. Angew. Chem., Int. Ed. Engl. 1986, 25, 478. Koziara, A.; Zwierzak, A. Synthesis 1992, 1063. Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114.
22. Brewster, P.; Hiron, F.; Hughes, E. D.; Ingold, C. K.; Rao, P. A. Nature 1950, 166, 178. Lieber, E.; Chao, T. S.; Rao, C. N. R. J. Org. Chem. 1957, 22, 238. Reeves, W. P.; Bahr, M. L. Synthesis 1976, 823. Nakajima, Y.; Kinishi, R.; Oda, J.; Inouye, Y. Bull. Chem. Soc. Jpn. 1977, 50, 2025. Jorapur, V. S.; Khalil, Z. H.; Duffley, R. P.; Razdan, R. K.; Martin, B. R.; Harris, L. S.; Dewey, W. L. J. Med. Chem. 1985, 28, 783. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. Hassner, A.; Stern M. Angew. Chem., Int. Ed. Engl. 1986, 25, 478. Koziara, A.; Zwierzak, A. Synthesis 1992, 1063. Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114.
23. Corey, E. J.; Nicolaou, K. C.; Balanson, R. D.; Machida, Y. Synthesis 1975, 590.
24. Smith, P. A. S. In Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds; Benjamin/Cummings: Reading, MA, 1983; p263.
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28. 3 in DMSO at 95 C was reported to be 1.5 mol/L, see: Wu, M.-C.; Anderson, L.; Slife, C. W.; Jensen, L. J. J. Org. Chem. 1974, 20, 3014.
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31. Alvarez, S. G.; Fisher, G. B.; Singaram, B. Presented at the 30th Western Regional American Chemical Society (ACS) Meeting and Pacific Conference, Sacramento, CA, Oct. 1994; paper 75.