General solution to the synthesis of N-2-substituted 1,2,3-triazoles

Organic Letters

Volumn 12, Issue 20, 2010, Pages 4632-4635

  Wang, Xiao Jun ^a   Zhang, Li ^a   Krishnamurthy, Dhileepkumar ^a   Senanayake, Chris H ^a   Wipf, Peter ^b  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TRIAZOLE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; STATIC ELECTRICITY; SYNTHESIS;

ALKYLATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STATIC ELECTRICITY; TRIAZOLES;

EID: 77957847870     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101965a     Document Type: Article

References (42)

1. Michael, A. J. Prakt. Chem. 1893, 48, 94-95
2. Wamhoff, H. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 5, p 669.
3. Dehne, H. In Methoden der Organischen Chemie (Houben-Weyl); Schumann, E., Ed.; Thieme: Stuttgart, 1994; Vol. E8d, pp 305 - 405.
4. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128-1137
5. Huisgen, R. 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984.
6. Kolb, H. C.; Fin, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021
7. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
8. Wu, P.; Fokin, V. V. Aldrichimica Acta 2007, 40, 7-17
9. Boren, B. C.; Narayan, S.; Rasmussen, L. K.; Zhang, L.; Zhao, H.; Lin, Z.; Jia, G.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 8923-8930
10. Tornǿe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
11. Katritzky, A. R.; Singh, S. K. J. Org. Chem. 2002, 67, 9077-9079
12. Majireck, M. M.; Weinreb, S. J. Org. Chem. 2006, 71, 8680-8683
13. Zhang, L.; Chen, X.; Xue, P.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G. J. Am. Chem. Soc. 2005, 127, 15998-15999
14. Kalisiak, J.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2008, 10, 3171-3174
15. Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 7786-7787
16. Chen, Y.; Liu, Y.; Petersen, J. L.; Shi, X. Chem. Commun. 2008, 3254-3256
17. Iddon, B.; Nicholas, M. J. Chem. Soc., Perkin Trans. 1 1996, 1341-1347
18. Kim, D. K.; Kim, J.; Park, H. J. Bioorg. Med. Chem. Lett. 2004, 14, 2401-2405
19. 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, 2109-2112
20. Koren, A. O. J. Heterocycl. Chem. 2002, 39, 1111-1112
21. For examples on N -2 arylation, see
22. Liu, Y.; Yan, W.; Chen, Y.; Petersen, J. L.; Shi, X. Org. Lett. 2008, 10, 5389-5392
23. 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, 5487-5491 For examples on the N -2 alkylation, acetylation, or arylation of 5-arylated, 4-alkylated, or 4-acylated 1,2,3-triazoles, see: Shi, X. US patent 2010/0069644 A1.
24. Wang, X.-H.; Zhang, Li.; Lee, H.; Haddad, N.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2009, 11, 5026-5028
25. Wang, X.-J.; Sidhu, K.; Zhang, Li.; Campbell, S.; Haddad, N.; Reeves, D. C.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2009, 11, 5490-5493
26. Iddon, B.; Nicholas, M. J. J. Chem. Soc., Perkin Trans. 1 1996, 1341-1347
27. Hosomi, A.; Iijima, S.; Sakurai, H. Chem. Lett. 1981, 243-246
28. Dichloro-1,2,3-triazole could not be prepared either by treatment of 1 with NCS or by the treatment of 5 with NCS.
29. iPrMgCl·LiCl, see
30. Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302-4320
31. For examples, see
32. Ohta, S.; Kawasaki, I.; Uemura, T.; Yamashita, M.; Yoshioka, T.; Yamaguchi, S. Chem. Pharm. Bull. 1997, 45, 1140-1145
33. Begtrup, M.; Larsen, P. Acta Chem. Scand. 1990, 44, 1050-1057
34. Spartan 08, v.1.21; Wavefunction, Inc.: Irvine, CA was used; all calculations were performed at the RB3LYP/6-311G* level.
35. Albert, A.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1989, 1903-1905
36. For regioselective N -2 glycosylation and hydroxyformylation, see
37. Sanghvi, Y. S.; Bhattacharya, B. K.; Kini, G. D.; Matsumoto, S. S.; Larson, S. B.; Jolley, W. B.; Robins, R. K.; Revankar, G. R. J. Med. Chem. 1990, 33, 336-344
38. See ref 4a.
39. For nonregioselective examples, see
40. Tom, A. C. In Sciences of Synthesis; Storr, R. C.; Gilchrist, T. L., Eds.; Thieme: Stuttgart, NY, 2004; Vol. 13, p 415.
41. De Meijere, A.; Diederich, F., Eds. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004
42. Handbook of Organopalladium Chemistry; Negishi, E., Ed.; Wiley-Interscience: New York, 2002.