Synthesis of 1,4-disubstituted 1,2,3-triazoles via click reaction in micro flow reactor

Heterocycles

Volumn 8, Issue 2, 2014, Pages 1511-1517

  Lei, Ming ^a,b   Hu, Ruijun ^a   Wang, Yanguang ^a   Zhang, Hong ^b,c  

^a ZHEJIANG UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY   (China)

^c ZHEJIANG UNIVERSITY SCHOOL OF MEDICINE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84986538293     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-13-S(S)51     Document Type: Article

References (43)

1. R. Huisgen In 1,3-dipolar cycloaddition chemistry; ed. by A. Padwa; Wiley: New York, 1984.
2. (a) V. V. Rostovstev, L. G. Green, V. V. Fokin, and K. B. Sharpless, Angew. Chem. Int. Ed., 2002, 41, 2596
3. (b) V. O. Rodionov, V. V. Fokin, and M. G. Finn, Angew. Chem. Int. Ed., 2005, 44, 2210
4. (c) B. H. Lipshutz and B. R. Taft, Angew. Chem. Int. Ed., 2006, 45, 8235
5. (d) S. Díez-González, A. Correa, L. Cavallo, and S. P. Nolan, Chem. Eur. J., 2006, 12, 7558
6. (e) T. R. Chan, R. Hilgraf, K. B. Sharpless, and V. V. Fokin, Org. Lett., 2004, 6, 2853
7. (f) C. Girard, E. Önen, M. Aufort, S. Beauvière, E. Samson, and J. Herscovici, Org. Lett., 2006, 8, 1689
8. (g) S. Chassaing, M. Kumarraja, A. S. S. Sido, P. Pale, and J. Sommer, Org. Lett., 2007, 9, 883
9. (h) F. Alonso, Y. Moglie, G. Radivoy, and M. Yus, Eur. J. Org. Chem., 2010, 1875
10. (i) C. Z. Tao, X. Cui, J. Li, A. X. Liu, L. Liu, and Q. X. Guo, Tetrahedron Lett., 2007, 48, 3525
11. (j) I. S. Park, M. S. Kwon, Y. Kim, J. S. Lee, and J. Park, Org. Lett., 2008, 10, 497
12. (k) J. E. Hein and V. V. Fokin, Chem. Soc. Rev., 2010, 39, 1302.
13. (a) A. Devadoss and C. E. D. Chidsey, J. Am. Chem. Soc., 2007, 129, 5370
14. (b) L. V. Lee, M. L. Mitchell, S. J. Huang, V. V. Fokin, K. B. Sharpless, and C. H. Wong, J. Am. Chem. Soc., 2003, 125, 9588
15. (c) T. S. Seo, Z. Li, H. Ruparel, and J. Ju, J. Org. Chem., 2003, 68, 609
16. (d) Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, and M. G. Finn, J. Am. Chem. Soc., 2003, 125, 3192
17. (e) H. Struthers, B. Spingler, T. L. Mindt, and R. Schibli, Chem. Eur. J., 2008, 14, 6173
18. (f) J. Shen, R. Woodward, J. P. Kedenburg, X. W. Liu, M. Chen, L. Y. Fang, D. X. Sun, and P. G. Wang, J. Med. Chem., 2008, 51, 7417
19. (g) J. F. Lutz and Z. Zarafshani, Adv. Drug Delivery Rev., 2008, 60, 958.
20. (a) P. Appukkuttan, W. Dehaen, V. V. Fokin, and E. V. der Eycken, Org. Lett., 2004, 6, 4223
21. (b) A. K. Feldman, B. Colasson, and V. V. Fokin, Org. Lett., 2004, 6, 3897
22. (c) H. Sharghi, R. Khalifeh, and M. M. Doroodmanda, Adv. Synth. Catal., 2009, 351, 207
23. (d) D. Yang, N. Fu, Z. L. Liu, Y. Li, and B. H. Chen, Synlett, 2007, 278
24. (e) D. Kumar and V. B. Reddy, Synthesis, 2010, 1687
25. (f) K. Kacprzak, Synlett, 2005, 943
26. (g) A. R. Bogdan and N. W. Sach, Adv. Synth. Catal., 2009, 351, 849
27. (h) F. Alonso, Y. Moglie, G. Radivoy, and M. Yusa, Adv. Synth. Catal., 2010, 352, 3208.
28. B. H. M. Kuijpers, S. Groothuys, A. C. Soede, P. Laverman, O. C. Boerman, F. L. van Delft, and F. P. J. T. Rutjes, Bioconjugate. Chem., 2007, 18, 1847.
29. (a) U. Sirion, H. J. Kim, J. H. Lee, J. W. Seo, B. S. Lee, S. J. Lee, S. J. Oh, and D. Y. Chi, Tetrahedron Lett., 2007, 48, 3953
30. (b) M. Glaser and E. G. Robins, J. Labelled Compd. Radiopharm., 2009, 52, 407
31. (c) C. Mamat, T. Ramenda, and F. R. Wuest, Mini-Rev. Org. Chem., 2009, 6, 21
32. (d) M. Lei, M. Tian, and H. Zhang, Curr. Med. Imaging Rev., 2012, 8, 302.
33. (a) L. Kang, B. G. Chung, R. A. Langer, and A. Khademhosseini, Drug Discovery Today, 2008, 13, 1
34. (b) C. O. Kappe and D. Dallinger, Nature Rev. Drug Discovery, 2006, 5, 51
35. (c) C. Wiles and P. Watts, Expert Opin. Drug Discovery, 2007, 11, 1487.
36. (a) B. P. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan, and D. T. McQuade, Chem. Rev., 2007, 107, 2300
37. (b) I. R. Baxendale, J. J. Hayward, S. Lanners, S. V. Ley, and C. D. Smith, 'Microreactors in Organic Synthesis and Catalysis,' ed. by T. Wirth, Wiley-VCH, Weinheim, 2008
38. (c) W. Ehrfeld, V. Hessel, and H. Lowe, 'Microreactors: New Technology for Modern Chemistry,' Wiley, Weinheim, 2000
39. (d) C. M. Griffiths-Jones, M. D. Hopkin, D. Jönsson, S. V. Ley, D. J. Tapolczay, E. Vickerstaffe, and M. Ladlow, J. Comb. Chem., 2007, 9, 422.
40. (a) R. J. Hu, M. Lei, H. S. Xiong, X. Mu, Y. G. Wang, and X. F. Yin, Tetrahedron Lett., 2008, 49, 387
41. (b) M. Lei, W. Tian, R. J. Hu, W. Li, and H. Zhang, Synthesis, 2012, 44, 2519
42. (c) M. Lei, W. Li, R. J. Hu, W. Tian, Y. G. Wang, and H. Zhang, Heterocycles, 2012, 86, 777.
43. J. Gao, X. F. Yin, and Z. L. Fang, Lab Chip, 2004, 4, 47.