Direct synthesis of acyl azides from carboxylic acids by the combination of trichloroacetonitrile, triphenylphosphine and sodium azide

Synlett

Volumn , Issue 13, 2008, Pages 2072-2074

  Kim, Joong Gon ^a   Jang, Doo Ok ^b  

^a Hanwha Corporation   (South Korea)

^b Yonsei University Wonju   (South Korea)

Author keywords

Acylations; Azides; Carboxylic acids; Peptides; Trichloroacetonitrile

Indexed keywords

ACETONITRILE DERIVATIVE; AZIDE; CARBOXYLIC ACID; SODIUM AZIDE; TRICHLOROACETIC ACID; TRIPHENYLPHOSPHINE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 49649124168     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1077979     Document Type: Article

References (28)

1. (a) Lowski, W. In Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic: Orlando, 1984, 205-246.
2. (b) Moore, H. W.; Goldfish, D. M. In The Chemistry of Halides, PseudoHalides and Azides, Vol. 1; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1983, 321-368.
3. (c) Patai, S. The Chemistry of the Azido Group; Wiley Interscience: Chichester, 1971, 397-405.
4. (a) Jones, J. The Chemical Synthesis of Peptides; Clarendon Press: Oxford, 1991.
5. (b) Meienhofer, J. The Peptides, Vol. 1; Academic Press: New York, 1979.
6. (c) Vommina, V.; Suresh Babu, V. V. S.; Ananda, K.; Vasanthakumar, G.-R. J. Chem. Soc., Perkin Trans, 1 2000, 4328.
7. (a) Frøyen, P. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 78, 161.
8. (b) Rawal, V. H.; Zhong, H. I. Tetrahedron Lett. 1994, 35, 4947.
9. (c) Sakai, K.; Anselme, J.-P. J. Org. Chem. 1971, 36, 2387.
10. (d) Van Reijendam, J. W.; Baardman, F. Synthesis 1973, 413.
11. (e) Prakash, G. K. S.; Iyer, P. S.; Arvanaghi, M.; Olah, G. A. J. Org. Chem. 1983, 48, 3358.
12. (f) Poster, J. R.; Wymann, W. E. Synthesis 1983, 38.
13. (g) Ongeri, S.; Aitken, D.; Husson, H.-P. Synth. Commun. 2000, 30, 2593.
14. Lee, J. G.; Kwak, K. H. Tetrahedron Lett. 1992, 33, 3165.
15. Marinescu, L.; Thinggaard, J.; Thomsen, I.; Bols, M. J. Org. Chem. 2003, 68, 9453.
16. Chiyoda, T.; Iida, K.; Takatori, K.; Kajiwara, M. Synlett 2000, 1427.
17. El-Faham, A.; Abdul-Ghani, M. Org. Prep. Proced. Int. 2003, 35, 369.
18. Lago, J. M.; Arrieta, A.; Palomo, C. Synth. Commun. 1983, 13, 289.
19. Arrieta, A.; Aizpurua, J. M.; Palomo, C. Tetrahedron Lett. 1984, 25, 3365.
20. (a) Gumaste, V. K.; Bhawal, B. M.; Deshmukh, A. R. A. S. Tetrahedron Lett. 2002, 43, 1345.
21. (b) Bao, W.; Wang, Q. J. Chem. Res., Synop. 2003, 700.
22. Bandgar, B. P.; Pandit, S. S. Tetrahedron Lett. 2002, 43, 3413.
23. Frøyen, P. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 89, 57.
24. Jang, D. O.; Park, D. J.; Kim, J. Tetrahedron Lett. 1999, 40, 5323.
25. 4. After filtration, the solvent was removed and the residue was purified by column chromatography on silica gel (hexanes-EtOAc, 2:1) to give benzoyl azide (141 mg, 96%).
26. 3): δ = 1.41 (d, J = 2.2 Hz, 3 H), 3.86 (m, 1 H), 4.22 (t, J = 2.3 Hz, 1 H), 4.41 (d, J = 2.3 Hz, 2 H), 5.28 (s, 1 H), 7.22-7.84 (m, 8 H).
27. 3): δ = 0.92 (s, 6 H), 1.42 (d, J = 2.2 Hz, 3 H), 1.55 (m, 1 H), 1.64 (m, 2 H), 3.71 (s, 3 H), 4.23 (t, J = 2.4 Hz, 1 H), 4.30 (t, J = 2.2 Hz, 1 H), 4.40 (d, J = 2.4 Hz, 2 H), 4.61 (q, J = 1.6 Hz, 1 H), 5.42 (s, 1 H), 6.37 (s, 1 H), 7.25-7.82 (m, 8 H).
28. Cho, D. H.; Jang, D. O. Tetrahedron Lett. 2004, 45, 2285.