Parallel Synthesis of Strongly Fluorescent Tetraaryl-4,5-dihydro-1,2,4-triazoles via 1,3-Dipolar Cycloaddition on Soluble Polymer Support

Wang-Ge Shou; Yun-Yun Yang; Yan-Guang Wang

doi:10.1055/s-2005-918430

PAPER

Parallel Synthesis of Strongly Fluorescent Tetraaryl-4,5-dihydro-1,2,4-triazoles via 1,3-Dipolar Cycloaddition on Soluble Polymer Support

Wang-Ge Shou, Yun-Yun Yang, Yan-Guang Wang*
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87951512; e-Mail: orgwyg@zju.edu.cn;

Abstract

All articles of this category

Abstract

An efficient liquid-phase synthesis of strongly fluorescent tetraaryl-4,5-dihydro-1,2,4-triazoles via 1,3-dipolar cycloaddition of imines with nitrile imines generated in situ on soluble polymer support is described.

Key words

liquid-phase synthesis - 4,5-dihydro-1,2,4-triazole - 1,3-dipolar cycloaddition - nitrile imine - fluorescent - poly(ethylene glycol) (PEG)

Full Text

References

1a Nefzi A. Ostresh JM. Yu JP. Houghten RA. J. Org. Chem. 2004, 69: 3603

1b Combinatorial Chemistry and Molecular Diversity in Drug Discovery Gorden EM. Kerwin J. F Jr. Wiley; New York: 1998.

1c Hall DG. Manku S. Wang F. J. Comb. Chem. 2001, 3: 125

1d Dolle RE. J. Comb. Chem. 2001, 3: 477

1e Schiedel M.-S. Briehn CA. Bäuerle P. Angew. Chem. Int. Ed. 2001, 40: 4677

2a Gallop MA. Barrett RW. Dower WJ. Fodor SPA. Gordon EM. J. Med. Chem. 1994, 37: 1233

2b Keating TA. Armsrong RW. J. Am. Chem. Soc. 1996, 118: 2574

3a Gravert EM. Janda KD. Chem. Rev. 1997, 97: 489

3b Wentworth P. Janda KD. Chem. Commun. 1999, 1917

3c Lee MJ. Sun C.-M. Tetrahedron Lett. 2004, 45: 437

3d Toy PH. Janda KD. Acc. Chem. Res. 2000, 33: 546

3e Yeh C.-M. Tung C.-L. Sun C.-M. J. Comb. Chem. 2000, 2: 341

3f Yeh WB. Sun CM. J. Comb. Chem. 2004, 6: 279

3g Bendale PM. Sun C.-M. J. Comb. Chem. 2002, 4: 359

4a Harwing CW. Garvert DJ. Janda KD. Chemtracts: Org. Chem. 1999, 12: 1

4b Vandersteen AM. Han H. Janda KD. Mol. Diversity 1996, 2: 89

4c Annunziata R. Benaglia M. Cinquini M. Cozzi F. Chem. Eur. J. 2000, 6: 133

4d Luisa G. Giorgio M. Pietro C. J. Chem. Soc. Perkin Trans. 1 2002, 2504

4e Chen SQ. Janda KD. J. Am. Chem. Soc. 1997, 119: 8724

4f Horl M. Janda KD. J. Org. Chem. 1998, 63: 889

5 Collin X. Sauleau A. Coulon J. Bioorg. Med. Chem. Lett. 2003, 13: 2601

6 Papakonstantiou-Garoufalias S. Pouli N. Marakos P. Chytyroglou-Ladas A. Il Farmaco 2002, 57: 973

7 Jenkins SM. Wadsworth H. Brmidge S. Orlek BS. Wyman PA. Riley GJ. Hawkins J. J. Med. Chem. 1992, 35: 2392

8a Enas MA. Nehal ME. Hamdi MH. Helv. Chim. Acta 2002, 85: 320

8b Xu JX. Wang CB. Zhang QH. Heteroat. Chem. 2001, 12: 557

8c Aversa MC. Ferlazzo A. Giannetto P. Kohnke FH. Synthesis 1986, 230

9a Cui SL. Lin XF. Wang YG. J. Org. Chem. 2005, 70: 2866

9b Xia M. Wang YG. Tetrahedron Lett. 2002, 43: 7703

9c Shang YJ. Wang YG. Synthesis 2002, 1663

9d Lin XF. Zhang J. Wang YG. Tetrahedron Lett. 2003, 44: 4113

9e Shang YJ. Wang YG. Chin. J. Chem. 2003, 21: 7 ; Chem. Abstr. 2003, 138: 368689

9f Shang YJ. Shou WG. Wang YG. Synlett 2003, 1064

9g Lin XF. Zhang J. Cui SL. Wang YG. Synthesis 2003, 1569

9h Shang YJ. Wang YG. Tetrahedron Lett. 2002, 43: 2247

10a Petel HV. Vyas KA. Pandey KA. Pandey SP. Fernandes S. Tetrahedron 2000, 56: 8071

10b Shawali AS. Gomha SM. Tetrahedron 2002, 58: 8559

10c Paulvannan K. Hale R. Sedehi D. Chen T. Tetrahedron 2001, 57: 9677

11 Schiedel MS. Briehn CA. Bauerle P. Angew. Chem. Int. Ed. 2001, 40: 4677

12 Demas JN. Grosby GA. J. Phys. Chem. 1971, 75: 991

13 Schmitz C. Posch P. Thelakkat M. Schmidt HW. Phys. Chem. Chem. Phys. 1999, 1: 1777