SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 13, 2009, Pages 2162-2166

'Click' chemistry on sugar-derived alkynes: A tandem 'click-click' approach to bistriazoles

(3) Kaliappan, Krishna P a Kalanidhi, Palanichamy a Mahapatra, Subham a

a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY (India)

Author keywords

'Click' reaction; Alkyne; Azide; Azido alkyne; Bistriazole; C glycoside; Triazole

Indexed keywords

ALKYNE DERIVATIVE; BISTRIAZOLE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 68949156523 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217570 Document Type: Article

Times cited : (23)

References (53)

1
- 12944306056
- Elsevier: New York
- (a) Meo, P.; Osborn, H. M. I. Best Synthetic Methods: Carbohydrates; Elsevier: New York, 2003, 337-384.
- (2003) Best Synthetic Methods: Carbohydrates , pp. 337-384
- Meo, P.¹ Osborn, H.M.I.²

2
- 0004231915
- CRC Press: Boca Raton
- (b) Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, 1995.
- (1995) C-Glycoside Synthesis
- Postema, M.H.D.¹

3
- 0003522385
- Pergamon: Tarrytown, NY
- (c) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon: Tarrytown / NY, 1995.
- (1995) The Chemistry of C-Glycosides
- Levy, D.E.¹ Tang, C.²

4
- 29444442296
- For reviews on C-glycoside synthesis, see: a
- For reviews on C-glycoside synthesis, see: (a) Lin, C.-H.; Lin, H.-C.; Yang, W.-B. Curr. Top. Med. Chem. 2005, 5, 1431.
- (2005) Curr. Top. Med. Chem , vol.5 , pp. 1431
- Lin, C.-H.¹ Lin, H.-C.² Yang, W.-B.³

5
- 29444436667
- (b) Yuan, X.; Linhardt, R. J. Curr. Top. Med. Chem. 2005, 5, 1393.
- (2005) Curr. Top. Med. Chem , vol.5 , pp. 1393
- Yuan, X.¹ Linhardt, R.J.²

6
- 29444458427
- (c) Lee, D. Y. W.; He, M. Curr. Top. Med. Chem. 2005, 5, 1333.
- (2005) Curr. Top. Med. Chem , vol.5 , pp. 1333
- Lee, D.Y.W.¹ He, M.²

7
- 0034746037
- (d) Somsak, L. Chem. Rev. 2001, 101, 81.
- (2001) Chem. Rev , vol.101 , pp. 81
- Somsak, L.¹

8
- 0034507032
- (e) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395.
- (2000) Chem. Rev , vol.100 , pp. 4395
- Dondoni, A.¹ Marra, A.²

9
- 0032552046
- (f) Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913.
- (1998) Tetrahedron , vol.54 , pp. 9913
- Du, Y.¹ Linhardt, R.J.² Vlahov, I.R.³

10
- 0002476212
- (g) Beau, J. M.; Gallagher, T. Top. Curr. Chem. 1997, 187, 1.
- (1997) Top. Curr. Chem , vol.187 , pp. 1
- Beau, J.M.¹ Gallagher, T.²

11
- 33750477645
- For recent reviews on C-glycoside biology and biosynthesis, see: a
- For recent reviews on C-glycoside biology and biosynthesis, see: (a) Wellington, K. W.; Benner, S. A. Nucleosides, Nucleotides Nucleic Acids 2006, 25, 1309.
- (2006) Nucleosides, Nucleotides Nucleic Acids , vol.25 , pp. 1309
- Wellington, K.W.¹ Benner, S.A.²

12
- 29244446754
- (b) Bililign, T.; Griffith, B. R.; Thorson, J. S. Nat. Prod. Rep. 2005, 22, 742.
- (2005) Nat. Prod. Rep , vol.22 , pp. 742
- Bililign, T.¹ Griffith, B.R.² Thorson, J.S.³

13
- 29444451430
- (c) Zou, W. Curr. Top. Med. Chem. 2005, 5, 1363.
- (2005) Curr. Top. Med. Chem , vol.5 , pp. 1363
- Zou, W.¹

14
- 29444458427
- (c) Lee, D. Y. W.; He, M. Curr. Top. Med. Chem. 2005, 5, 1333.
- (2005) Curr. Top. Med. Chem , vol.5 , pp. 1333
- Lee, D.Y.W.¹ He, M.²

15
- 29444453052
- (e) Hultin, P. G. Curr. Top. Med. Chem. 2005, 5, 1299.
- (2005) Curr. Top. Med. Chem , vol.5 , pp. 1299
- Hultin, P.G.¹

16
- 0035171364
- (f) Compain, P.; Martin, O. R. Bioorg. Med. Chem. 2001, 9, 3077.
- (2001) Bioorg. Med. Chem , vol.9 , pp. 3077
- Compain, P.¹ Martin, O.R.²

17
- 0002212956
- (g) Nicotra, F. Top. Curr. Chem. 1997, 187, 55.
- (1997) Top. Curr. Chem , vol.187 , pp. 55
- Nicotra, F.¹

18
- 0028063421
- Alvarez, R.; Velazquez, S.; San-Felix, A.; Aquaro, S.; De Clercq, E.; Perno, C. F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. J. Med. Chem. 1994, 37, 4185.
- (1994) J. Med. Chem , vol.37 , pp. 4185
- Alvarez, R.¹ Velazquez, S.² San-Felix, A.³ Aquaro, S.⁴ De Clercq, E.⁵ Perno, C.F.⁶ Karlsson, A.⁷ Balzarini, J.⁸ Camarasa, M.J.⁹

19
- 0034624685
- 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.; Yagi, B. H. J. Med. Chem. 2000, 43, 953.
- (2000) J. Med. Chem , vol.43 , pp. 953
- Genin, M.J.¹ Allwine, D.A.² Anderson, D.J.³ Barbachyn, M.R.⁴ Emmert, D.E.⁵ Garmon, S.A.⁶ Graber, D.R.⁷ Grega, K.C.⁸ Hester, J.B.⁹ Hutchinson, D.K.¹⁰ Morris, J.¹¹ Reischer, R.J.¹² Ford, C.W.¹³ Zurenko, G.E.¹⁴ Hamel, J.C.¹⁵ Schaadt, R.D.¹⁶ Stapert, D.¹⁷ Yagi, B.H.¹⁸

20
- 34247237682
- (a) Lutz, J.-F. Angew. Chem. Int. Ed. 2007, 46, 1018.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 1018
- Lutz, J.-F.¹

21
- 0348109450
- (b) Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128.
- (2003) Drug Discovery Today , vol.8 , pp. 1128
- Kolb, H.C.¹ Sharpless, K.B.²

22
- 0344443730
- (c) Breinbauer, R.; Koehn, M. ChemBioChem 2003, 4, 1147.
- (2003) ChemBioChem , vol.4 , pp. 1147
- Breinbauer, R.¹ Koehn, M.²

23
- 0036127307
- Dalvie, D. K.; Kalgutkar, A. S.; Khojasteh-Bakht, S. C.; Obach, R. S.; O'Donnell, J. P. Chem. Res. Toxicol. 2002, 15, 269.
- (2002) Chem. Res. Toxicol , vol.15 , pp. 269
- Dalvie, D.K.¹ Kalgutkar, A.S.² Khojasteh-Bakht, S.C.³ Obach, R.S.⁴ O'Donnell, J.P.⁵

24
- 84981452695
- (a) Hüisgen, R.; Szeimies, G.; Moebius, L. Chem. Ber. 1967, 100, 2494.
- (1967) Chem. Ber , vol.100 , pp. 2494
- Hüisgen, R.¹ Szeimies, G.² Moebius, L.³

25
- 0004101860
- Padwa, A, Ed, Wiley: New York
- (b) Hüisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984, 1-176.
- (1984) 1,3-Dipolar Cycloaddition Chemistry , pp. 1-176
- Hüisgen, R.¹

26
- 0037099395
- (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 2596
- Rostovtsev, V.V.¹ Green, L.G.² Fokin, V.V.³ Sharpless, K.B.⁴

27
- 0037012920
- (b) Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
- (2002) J. Org. Chem , vol.67 , pp. 3057
- Tornoe, C.W.¹ Christensen, C.² Meldal, M.³

28
- 68949123388
- For an updated list, see
- For an updated list, see: http://www.scripps.edu/chem/sharpless/click. html

29
- 34547272503
- Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249.
- (2007) Chem. Soc. Rev , vol.36 , pp. 1249
- Moses, J.E.¹ Moorhouse, A.D.²

30
- 33744908340
- For selected examples, see: a
- For selected examples, see: (a) Giguere, D.; Patnam, R.; Bellefleur, M.-A.; St-Pierre, C.; Sato, S.; Roy, R. Chem. Commun. 2006, 2379.
- (2006) Chem. Commun , pp. 2379
- Giguere, D.¹ Patnam, R.² Bellefleur, M.-A.³ St-Pierre, C.⁴ Sato, S.⁵ Roy, R.⁶

31
- 21344450055
- (b) Dorner, S.; Westermann, B. Chem. Commun. 2005, 2852.
- (2005) Chem. Commun , pp. 2852
- Dorner, S.¹ Westermann, B.²

32
- 4444268846
- (c) Dondoni, A.; Giovannini, P. P.; Massi, A. Org. Lett. 2004, 6, 2929.
- (2004) Org. Lett , vol.6 , pp. 2929
- Dondoni, A.¹ Giovannini, P.P.² Massi, A.³

33
- 0141629513
- (c) Perez-Balderas, F.; Ortega-Munoz, M.; Morales-Sanfrutos, J.; Hernandez-Mateo, F.; Calvo-Flores, F. G.; Calvo-Asin, J. A.; Isac-Garcia, J.; Santoyo-Gonzalez, F. Org. Lett. 2003, 5, 1951.
- (2003) Org. Lett , vol.5 , pp. 1951
- Perez-Balderas, F.¹ Ortega-Munoz, M.² Morales-Sanfrutos, J.³ Hernandez-Mateo, F.⁴ Calvo-Flores, F.G.⁵ Calvo-Asin, J.A.⁶ Isac-Garcia, J.⁷ Santoyo-Gonzalez, F.⁸

34
- 0037021535
- (e) Fazio, F.; Bryan, M. C.; Blixt, O.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 2002, 124, 14397.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 14397
- Fazio, F.¹ Bryan, M.C.² Blixt, O.³ Paulson, J.C.⁴ Wong, C.-H.⁵

35
- 33747873539
- Cheshev, P.; Marra, A.; Dondoni, A. Org. Biomol. Chem. 2006, 4, 3225.
- (2006) Org. Biomol. Chem , vol.4 , pp. 3225
- Cheshev, P.¹ Marra, A.² Dondoni, A.³

36
- 33748047478
- (a) Montagnet, O. D.; Lessene, G.; Hughes, A. B. Tetrahedron Lett. 2006, 47, 6971.
- (2006) Tetrahedron Lett , vol.47 , pp. 6971
- Montagnet, O.D.¹ Lessene, G.² Hughes, A.B.³

37
- 29044447377
- (b) Angelo, N. G.; Arora, P. S. J. Am. Chem. Soc. 2005, 127, 17134.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 17134
- Angelo, N.G.¹ Arora, P.S.²

38
- 41549083761
- (a) Marra, A.; Moni, L.; Pazzi, D.; Corallini, A.; Bridi, D.; Dondoni, A. Org. Biomol. Chem. 2008, 6, 1396.
- (2008) Org. Biomol. Chem , vol.6 , pp. 1396
- Marra, A.¹ Moni, L.² Pazzi, D.³ Corallini, A.⁴ Bridi, D.⁵ Dondoni, A.⁶

39
- 38049100206
- (b) Ornelas, C.; Aranzaes, J. R.; Salmon, L.; Astruc, D. Chem. Eur. J. 2008, 14, 50.
- (2008) Chem. Eur. J , vol.14 , pp. 50
- Ornelas, C.¹ Aranzaes, J.R.² Salmon, L.³ Astruc, D.⁴

40
- 33749138877
- (c) Dondoni, A.; Marra, A. J. Org. Chem. 2006, 71, 7546.
- (2006) J. Org. Chem , vol.71 , pp. 7546
- Dondoni, A.¹ Marra, A.²

41
- 33645814833
- (d) Fernandez-Megia, E.; Correa, J.; Rodriguez-Meizoso, I.; Riguera, R. Macromolecules 2006, 39, 2113.
- (2006) Macromolecules , vol.39 , pp. 2113
- Fernandez-Megia, E.¹ Correa, J.² Rodriguez-Meizoso, I.³ Riguera, R.⁴

42
- 34447539753
- (a) Chandrasekhar, S.; Rao, C. L.; Nagesh, C.; Reddy, C. R.; Sridhar, B. Tetrahedron Lett. 2007, 48, 5869.
- (2007) Tetrahedron Lett , vol.48 , pp. 5869
- Chandrasekhar, S.¹ Rao, C.L.² Nagesh, C.³ Reddy, C.R.⁴ Sridhar, B.⁵

43
- 20344369760
- (b) Hotha, S.; Anegundi, R. I.; Natu, A. A. Tetrahedron Lett. 2005, 46, 4585.
- (2005) Tetrahedron Lett , vol.46 , pp. 4585
- Hotha, S.¹ Anegundi, R.I.² Natu, A.A.³

44
- 33750086062
- Aucagne, V.; Leigh, D. A. Org. Lett. 2006, 8, 4505.
- (2006) Org. Lett , vol.8 , pp. 4505
- Aucagne, V.¹ Leigh, D.A.²

45
- 33947604111
- Kaliappan, K. P.; Subrahmanyam, A. V. Org. Lett. 2007, 9, 1121.
- (2007) Org. Lett , vol.9 , pp. 1121
- Kaliappan, K.P.¹ Subrahmanyam, A.V.²

46
- 0344666674
- (a) Lan, P.; Berta, D.; Porco, J. A.; South, M. S.; Parlow, J. J. J. Org. Chem. 2003, 68, 9678.
- (2003) J. Org. Chem , vol.68 , pp. 9678
- Lan, P.¹ Berta, D.² Porco, J.A.³ South, M.S.⁴ Parlow, J.J.⁵

47
- 0030996786
- (b) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413.
- (1997) Synthesis , pp. 413
- Alvarez, S.G.¹ Alvarez, M.T.²

48
- 0038070880
- (c) Smith, P. A. S.; Brown, B. B. J. Am. Chem. Soc. 1951, 73, 2438.
- (1951) J. Am. Chem. Soc , vol.73 , pp. 2438
- Smith, P.A.S.¹ Brown, B.B.²

49
- 68949094687
- Typical procedure for the simple 'click' reaction: To a solution of alkyne 3 (0.050 g, 0.19 mmol) and azide 5 (0.026 g, 0.19 mmol) in MeCN (1.9 mL) were added CuI (0.0746 g, 0.38 mmol) and DIPEA (0.1 mL, 0.57 mmol) successively at r.t. After stirring for 30 min, the reaction was quenched by adding sat. aq NH4Cl (10 mL, The organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 20 mL, After washing with brine (20 mL, the organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give the crude product, which was purified by recrystallisation from CH2Cl2-hexanes. The mother liquor was further purified by column chromatography (hexanes-EtOAc, 1.5:1) to afford triazole 12 (0.065 g, 85, Rf, 0.62 (EtOAc-hexanes, 1:1, mp 155-157°C; [a]20D -83.880 (c 0.21, CHCl3, 1H NMR 400 MHz, CDCl 3
- 3: 388.1872; found: 388.1892.

50
- 40449124453
- (a) Kaliappan, K. P.; Ravikumar, V.; Pujari, S. A. J. Chem. Sci. 2008, 120, 205.
- (2008) J. Chem. Sci , vol.120 , pp. 205
- Kaliappan, K.P.¹ Ravikumar, V.² Pujari, S.A.³

51
- 30344437006
- (b) Kaliappan, K. P.; Ravikumar, V.; Pujari, S. A. Tetrahedron Lett. 2006, 47, 981.
- (2006) Tetrahedron Lett , vol.47 , pp. 981
- Kaliappan, K.P.¹ Ravikumar, V.² Pujari, S.A.³

52
- 13044305813
- (c) Yadav, J. S.; Chander, M. C.; Rao, C. S. Tetrahedron Lett. 1989, 30, 5455.
- (1989) Tetrahedron Lett , vol.30 , pp. 5455
- Yadav, J.S.¹ Chander, M.C.² Rao, C.S.³

53
- 68949102680
- Typical procedure for the double 'click' reaction: To methyl propiolate 32 (0.024 mL, 0.27 mmol) in MeCN (1.5 mL) was added CuI (0.105 g, 0.552 mmol) and DIPEA (0.147 mL, 0.82 mmol, The reaction mixture became a clear solution. The azido-alkyne 31 (0.050 g, 0.27 mmol) was added and the reaction was stirred for 1 h (reaction monitored by TLC, Then, azide 6 (0.27 mmol) was added and the reaction was stirred for 15 minutes. The reaction was quenched by the addition of sat. aq NH4Cl (10 mL, the organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 20 mL, After washing with brine (20 mL, the organic layer was dried over Na2SO4 and concentrated in vacuo to give the crude product, which was purified by recrystallization from CH2Cl 2-hexanes. The mother liquor was purified by column chromatography (hexanes-EtOAc, 1:1.5) to afford triazole 35 0.050 g, 46, Compound 35
- 2: 218.0861; found: 218.0865.

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