Chemoselective nitration of phenols with iert-butyl nitrite in solution and on solid support

Organic Letters

Volumn 11, Issue 18, 2009, Pages 4172-4175

  Koley, Dlpankar ^a   Colón, Olvia C ^a   Savlnov, Sergey N ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYL NITRITE; N-BUTYL NITRITE; NITRITE; PEPTIDE; PEPTIDE HYDROLASE; PHENOL DERIVATIVE; TYROSINE;

ARTICLE; CHEMISTRY; ENZYMOLOGY; METABOLISM; OXIDATION REDUCTION REACTION; PLANT VIRUS;

NITRITES; OXIDATION-REDUCTION; PEPTIDE HYDROLASES; PEPTIDES; PHENOLS; PLANT VIRUSES; TYROSINE;

EID: 70349140106     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901731w     Document Type: Article

References (36)

1. (a) Morise, H.; Shimomura, O.; Johnson, F. H.; Winant, J. Biochemistry 1974, 13, 2656-2662.
2. (b) Royer, C. A. Chem. Rev. 2006, 106, 17691784.
3. Sapsford, K. E.; Berti, L.; Medintz, I. L. Angew. Chem., Int. Ed. 2006, 45, 4562-4588.
4. (a) Meldal, M.; Breddam, K. Anal. Biochem. 1991, 195, 141-147.
5. (b) Filippis, V. D.; Frasson, R.; Fontana, A. Protein Sci. 2006, 15, 976986.
6. Filippis, V. D.; Draghi, A.; Frasson, R.; Grandi, C.; Musi, V.; Fontana, A.; Pastore, A. Protein Sci. 2007, 16, 1257-1265.
7. Ridd, J. H. Chem. Soc. Rev. 1991, 20, 149-165.
8. (a) Dove, M. F. A.; Manz, B.; Montgomery, J.; Pattenden, G.; Wood, S. A. J. Chem. Soc, Perkin Trans. 1 1998, 1589-1590.
9. (b) Ma, D.; Tang, W.; Kozikowski, A. P.; Lewin, N. E.; Blumberg, P. M. J.Org. Chem. 1999, 64, 6366-6373.
10. Samajdar, S.; Becker, F. F.; Banik, B. K. Tetrahedron Lett. 2000, 41, 8017-8020.
11. Laali, K. K.; Gettwert, V. J. J. Org. Chem. 2001, 66, 35-40.
12. (e) Dagade, S. P.; Kadam, V. S.; Dongare, M. K. Catal. Commun. 2002, 1., 67-70.
13. (f) Shi, M.; Cui, S.-C. Adv. Synth. Catal. 2003, 345, 1197-1202.
14. (g) Sun, H.-B.; Hua, R.; Yin, Y. J. Org. Chem. 2005, 70, 9071-9073.
15. (h) Selvam, J. J. P.; Rajesh, V. S. K.; Reddy, S. R.; Venkateswarlu, Y. Tetrahedron Lett. 2006, 47, 2507-2509, and references therein.
16. (a) Bruice, T. C.; Gregory, M. J.; Walters, S. L. J. Am. Chem. Soc. 1968, 90, 1612-1619.
17. (b) Vincent, J. P.; Lazdunski, M.; Delaage, M. Eur. J. Biochem. 1970, 12, 250-257.
18. Walters, S. L.; Bruice, T. C. J. Am. Chem. Soc. 1971, 93, 2269-2282.
19. (a) Robins, M. J.; Uznañski, B. Can. J. Chem. 1981, 59, 2608-2611.
20. (b) Chan, D. C. M.; Rosowsky, A. J. Org. Chem. 2005, 70, 1364-1368.
21. (a) Barrett, D.; Tanaka, A.; Harada, K.; Watabe, E.; Maki, K.; Ikeda, F. Bioorg. Med. Chem. Lett. 2001, 11, 1843-1849.
22. (b) Black, R. M.; Balkovec, J. M.; Nollstadt, M. K.; Dreikorn, S.; Barrizal, K. F.; Abruzzo, G. K. Bioorg. Med. Chem. Lett. 1997, 7, 2879-2884.
23. Devivar, R. V.; Drach, J. G.; Townsend, L. B. Bioorg. Med Chem. Lett- 1992, 2, 1105-1110.
24. Toth, G.; Russell, K. C.; Landis, G.; Kramer, T. H.; Fang, L.; Knapp, R.; Davis, P.; Burks, T. F.; Yamamura, H.-I; Hruby, V. J. J.Med. Chem. 1992, 35, 2384-2391.
25. Lide, D. R., Ed. CRC Handbook of Chemistry and Physics, 89th ed.; Physical Constants of Organic Compounds; CRC Press: Boca Raton, FL, 2009; [Online].
26. Darbeau, R. W.; Pease, R. S.; Perez, E. V. J. Org. Chem. 2002, 67, 2942-2947.
27. Santini, R.; Griffith, M. C.; Qi, M. Teffahedron Lett. 1998, 39, 8951-8954.
28. Cavelier, F. Tetrahedron: Asymmetry 1997, 8, 41-43.
29. Astolfi, P.; Panagiotaki, M.; Greci, L. Eur. J. Org. Chem. 2005, 3052-3059.
30. Cook, C. D.; Woodworm, R. C. J. Am. Chem. Soc. 1953, 75, 62426244.
31. Doyel, M. P.; Terpstra, J. W.; Pickering, R. A.; Lepoire, D. M. J Qrg. Chem. 1983, 48, 3379-3382.
32. Yang, R.; Jin, X.; Wang, W.; Fan, K.; Zhou, M. J. Phys. Chem. A 2005, 109, 4261-4266.
33. Bhatia, S. C.; Hall, J. H. J Phys. Chem. 1980, 84, 3255-3259.
34. Riebsomer, J. L. Chem. Rev. 1945, 36, 157-233.
35. Hodges, G. R.; Marwaha, J.; Paul, T.; Ingold, K. U. Chem Res. Toxicol, 2000, 13, 1287-1293.
36. Kapust, R. B.; Tözcer, J.; Copeland, T. D.; Waugh, D. S. Biochem. Biophys. Commun. 2002, 294, 949-955.