Cu(I)-catalyzed one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles via nucleophilic displacement and 1,3-dipolar cycloaddition

Tetrahedron Letters

Volumn 47, Issue 18, 2006, Pages 3055-3058

  Sreedhar, B ^a   Reddy, P Surendra ^a   Kumar, N Sailendra ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1,3 Dipolar cycloaddition; 1,4 Disubstituted 1,2,3 triazoles; CuI; PEG; Water

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 3 PHENYL 2 (4 PHENYL 1,2,3 TRIAZOL 1 YLMETHYL)ACRYLIC ACID METHYL ESTER; ACETIC ACID; ALKYNE DERIVATIVE; AZIDE; COPPER; MACROGOL; SODIUM DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CATALYST; CYCLOADDITION; DRUG SYNTHESIS; ENVIRONMENT; METHODOLOGY; RECYCLING;

EID: 33645869286     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.007     Document Type: Article

References (38)

1. Pandey G., Singh R.P., Gary A., and Singh V.K. Tetrahedron Lett. 46 (2005) 2137-2140
2. Werner B., and Domling A. Molecules 8 (2003) 53-66
3. Domling A., and Ugi I. Angew. Chem., Int. Ed. 39 (2000) 3169-3210
4. Weber L. Drug Discovery Today 7 (2002) 143-147
5. Buckle D.R., and Rockell C.J.M. J. Chem. Soc., Perkin Trans. 1 (1982) 627-630
6. Buckle D.R., Outred D.J., Rockell C.J.M., Smith H., and Spicer B.A. J. Med. Chem. 26 (1983) 251-254
7. Buckle D.R., Outred D.J., Rockell C.J.M., Smith H., and Spicer B.A. J. Med. Chem. 29 (1986) 2262-2267
8. Genin M.J., Allwine D.A., Anderson D.J., Barbachyn M.R., Emmert D.E., Garmon S.A., Graber D.R., Grega K.C., Hester J.B., Hutchinson D.K., Morris J., Reischer R.J., Ford C.W., Zurenko G.E., Hamel J.C., Schaadt R.D., Stapert D., and Yagi B.H. J. Med. Chem. 43 (2000) 953-970
9. Alvarez R., Velazquez S., San-Felix A., Aquaro S., De Clercq E., Perno C.F., Karlsson A., Balzarini J., and Camarasa M.J. J. Med. Chem. 37 (1994) 4185-4194
10. L'abbe G. Chem. Rev. 69 (1969) 345-363
11. Huisgen R. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry (1984), Wiley, New York 1-176 Chapter 1
12. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem. 114 (2002) 2708-2711
13. Chan T.R., Robert H., Sharpless K.B., and Fokin V.V. Org. Lett. 6 (2004) 2653-2855
14. Orgueira H.A., Fokas D., Isome Y., Chan P.C.M., and Baldino C.M. Tetrahedron Lett. 46 (2005) 2911 and references cited therein
15. Pachon L.D., Van Maarseveen J.H., and Rothenberg G. Adv. Synth. Catal. 347 (2005) 811-815
16. Feldman A.K., Colasson B., and Fokin V.V. Org. Lett. 6 (2004) 3897-3899
17. Prasad A., Wim D., Fokin V.V., and Eycken E.V. Org. Lett. 6 (2004) 4223-4225
18. Yan Z.Y., Zhao Y.B., Fan M.J., Liu W.M., and Liang M.Y. Tetrahedron 61 (2005) 9331-9337
19. Akimova G.S., Chistokletov V.N., and Petrov A.A. Zh. Org. Khim. 3 (1967) 968
20. Chem. Abstr. 67 (1967) 100071
21. Tanaka Y., and Miller S.I. J. Org. Chem. 38 (1973) 2708-2712
22. Li Z., Seo T.S., and Ju J. Tetrahedron Lett. 45 (2004) 3143-3179
23. Kamijo S., Jin T., Huo Z., and Yamamoto Y. J. Am. Chem. Soc. 125 (2003) 7786-7787
24. Reichardt C. Solvents and Solvent Effects in Organic Chemistry (1988), VCH, Weinheim, Germany
25. Brack A. Adv. Space Res. 24 (1999) 417-433
26. Heldebrant D., and Jessop P.G. J. Am. Chem. Soc. 125 (2003) 5600-5601
27. Chandrasekhar S., Narasimhulu Ch., Sulthana S.S., and Reddy N.R. Org. Lett. (2002) 4399-4401
28. Namboodri V.V., and Varma R.S. Green. Chem. 3 (2001) 146-148
29. Haimov A., and Neumann R. Chem. Commun. (2002) 876-878
30. Zhang Z.H., Yin L., Wang Y.M., Liu J.Y., and Li Y. Green Chem. 6 (2004) 563-565
31. Basavaiah D., Rao A.J., and Satyanarayana T. Chem. Rev. 103 (2003) 811-891 and references cited therein
32. Yadav J.S., Manoj Kumar G., Sushil Kumar P., Reddy B.V.S., and Sarma A.V.S. Tetrahedron Lett. 46 (2005) 2761-2764
33. Li J., Wang X., and Zhang Y. Tetrahedron Lett. 46 (2005) 5233-5237
34. 2 gave poor yields 55%, 40% and 36%, respectively.
35. 1H NMR spectrum of 3 revealed the olefinic proton of the triazole ring at δ 7.49 ppm as a singlet, which confirms the regioselective formation of 3. When using Cu(II) salts, the olefinic protons signals at δ 7.42, 7.38 for 1,5- and 1,4-disubstituted 1,2,3-triazole isomers, respectively.
36. Fahmi H., Timothy L., Rostovtsev V.V., Needileman L., Sharpless K.B., and Fokin V.V. J. Am. Chem. Soc. 127 (2005) 210-216
37. 2: C, 71.46; H, 5.37; N, 13.16. Found: C, 71.45; H, 5.31; N, 13.14.
38. After extraction of the product by ether, the mother liquor was reused for the second run with the same substrates. The result of the first cycle and subsequent cycles gave the products in consistent yields (86%, 80%, 82% and 80%).