Highly regioselective N-2 arylation of 4,5-dibromo-1,2,3-triazole: efficient synthesis of 2-aryltriazoles

Organic Letters

Volumn 11, Issue 21, 2009, Pages 5026-5028

  Wang, Xiao Jun ^a   Zhang, Li ^a   Lee, Heewon ^a   Haddad, Nizar ^a   Krishnamurthy, Dhileepkumar ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4,5 DIBROMO 1,2,3 TRIAZOLE; 4,5-DIBROMO-1,2,3-TRIAZOLE; BROMINATED HYDROCARBON; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; HYDROGENATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROCARBONS, BROMINATED; HYDROGENATION; MOLECULAR STRUCTURE; STEREOISOMERISM; TRIAZOLES;

EID: 70350678977     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9019875     Document Type: Article

References (19)

1. (a) Wamhoff, H. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergman: Oxford, UK, 1984; Vol.5, p 669.
2. (b) Dehne, H. In Methoden der Organischen Chemie (Houben-Weyl); Schumann, E., Ed.; Thieme: Stuttgart, Germany, 1994; Vol.E8d, p 305.
3. (c) Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128.
4. (a) Huisgen, R. 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984.
5. (b) Kolb, H. C.; Fin, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
6. (c) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
7. (d) Wu, P.; Fokin, V. V. Aldrichim. Acta 2007, 40, 7.
8. For recent development on selective synthesis of N-2 substututed triazoles, see: (a) Kalisiak, J.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2008, 10, 3171.
9. (b) Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 7786.
10. (c) Liu, Y.; Yan, W.; Chen, Y.; Petersen, J. L.; Shi, X. Org. Lett. 2008, 10, 5389.
11. (d) Chen, Y.; Liu, Y.; Petersen, J. L.; Shi, X. Chem. Commun. 2008, 3254.
12. Tang, W.; Hu, Y. Synth. Commun. 2006, 36, 2461.
13. (a) Lacerda, P. S. S.; Silva, A. M. G.; Tome, A. C.; Neves, M.; Silva, A. M. S.; Cavaleiro, J. A. S.; Llamas-Saiz, A. L. Angew. Chem., Int. Ed. 2006, 45, 5487.
14. (b) Revesz, L.; Di Padova, F. E.; Buhl, T.; Feifel, R.; Gram, H.; Hiestand, P.; Manning, U.; Wolf, R.; Zimmerlin, A. G. Bioorg. Med. Chem. Lett. 2002, 12, 2109.
15. (c) Kim, D. K.; Kim, J.; Park, H. J. Bioorg. Med. Chem. Lett. 2004, 14, 2405.
16. Iddon, B.; Nicholas, M. J. J. Chem. Soc., Perkin Trans. 1 1996, 1341.
17. Albini, A.; Bettinetti, G. F.; Minoli, G. J. Org. Chem. 1983, 48, 1080.
18. 2: C, 22.51; H, 0.71; N, 13.13. Found: C, 22.72; H, 0.60; N, 13.24.
19. + 161.0809, found 161.0821.