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Synthesis 2005(20): 3535-3540
DOI: 10.1055/s-2005-918430
DOI: 10.1055/s-2005-918430
PAPER
© Georg Thieme Verlag Stuttgart · New York
Parallel Synthesis of Strongly Fluorescent Tetraaryl-4,5-dihydro-1,2,4-triazoles via 1,3-Dipolar Cycloaddition on Soluble Polymer Support
Further Information
Received
10 May 2005
Publication Date:
25 October 2005 (online)
Publication History
Publication Date:
25 October 2005 (online)
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)
-
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