One-pot sequential synthesis of β-hydroxy-1,4-disubstituted-1,2,3- triazoles from in-situ generated β-azido alcohol by click chemistry

Synthetic Communications

Volumn 38, Issue 13, 2008, Pages 2158-2167

  Reddy, K Rajender ^a   Maheswari, C Uma ^a   Rajgopal, K ^a   Kantam, M Lakshmi ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1,2,3 triazole; 1,2 Azidol; Click reaction; Cycloaddition; Epoxide; Ring opening

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; ALCOHOL; ALKYNE; AZIDE; COPPER COMPLEX; CYCLOHEXANE OXIDE; EPOXIDE; WATER;

ARTICLE; CATALYST; CHEMICAL REACTION; CYCLOADDITION; ELECTROSPRAY MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SYNTHESIS;

EID: 46749100951     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802026329     Document Type: Article

References (16)

1. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
2. Winstein, S.; Henderson, R. B. In Heterocyclic Compounds, R. C. Elderfield, (Ed.); Wiley & Sons, Inc.: London, 1950, vol.1.
3. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry. A. Padwa. (Ed.); Wiley: New York, 1984, pp. 1-176.
4. (a) Fan, W. Q.; Katritzky, A. R. In Comprehensive Heterocyclic chemistry II, vol. 4; A. R. Katritzky, C. W. Rees, E. F. V.Scriven. (Eds.); Elsevier Science: Oxford, 1996, pp. 1-126;
5. (b) Holla, B. S.; Mahalinga, M.; Karthikeyan, M. S.; Poojary, B.; Akberali, P. M.; Kumari, N. S. Synthesis, characterization and antimicrobial activity of some substituted 1,2,3-triazoles. Eur. J. Med. Chem. 2005, 40, 1173-1178;
6. (c) Elmorsi, M. A.; Hassanein, A. M. Corrosion inhibition of copper by heterocyclic compounds. Corros. Sci. 1999, 41, 2337-2352;
7. (d) Kim, D. K.; Kim, J.; Perk, H. J. Synthesis and biological evaluation of novel 2-pyridinyl-[1,2,3]triazoles as inhibitors of transforming growth factor β 1 type 1 receptor. Bioorg. Med. Chem. Lett. 2004, 14, 2401-2405.
8. Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. Ring opening of epoxides with sodium azide in Water. A regioselective pH-controlled reaction. J. Org. Chem. 1999, 64, 6094-6096 and references therein.
9. (a) Saxon, E.; Bertozzi, C. R. Cell surface engineering by a modified Staudinger reaction. Science 2000, 287, 2007-2010;
10. (b) Kiick, K. L.; Saxon, E.; Tirrel, D. A.; Bertozzi, C. R. Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation. Proc. Natl Acad. Sci. USA 2002, 99, 19-24;
11. (c) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective ligation of azides and terminal alkynes. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
12. Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67, 3057-3064.
13. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V.V. Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates. J. Am. Chem. Soc. 2005, 127, 210-216.
14. Scriven, E. F. V.; Turnbull, K. Azides: their preparation and synthetic uses. Chem. Rev. 1988, 88, 297-368.
15. Rajender Reddy, K.; Rajgopal, K.; Lakshmi Kantam, M. Copper(II)-promoted regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles in water. Synlett. 2006, 6, 957-959.
16. Brik, A.; Alexandratos, J.; Lin, Y.-C.; Elder, J. H.; Olson, A. J.; Wlodawer, A.; Goodsell, D.S.; Wong, C. H. 1,2,3-Triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors. ChemBioChem 2005, 6, 1167-1169.