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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 9
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Original Articles

Stereoselective Synthesis of Phenyl-1,2,3-triazoles Containing (E)-Vinyl Halide Group via a One-Pot, Three-Component Reaction

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Pages 1267-1275 | Received 01 Sep 2009, Published online: 30 Mar 2011

REFERENCES

  • Katritzky , A. R. ; Zhang , Y. ; Singh , S. K. 1,2,3-Triazole formation under mild conditions via 1,3-dipolar cycloaddition of acetylenes with azides . Heterocycles 2003 , 60 , 1225 – 1239 .
  • (a) Tornøe , C. W. ; Christensen , C. ; Meldal , M. J. 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 ; (b) 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 .
  • Kolb , H. C. ; Sharpless , K. B. The growing impact of click chemistry on drug discovery. Drug Discov. Today 2003, 8, 1128–1137.
  • (a) Wu , P. ; Feldman , A. K. ; Nugent , A. K. ; Hawker , C. J. ; Scheel , A. ; Voit , B. ; Pyun , J. ; Frechet , J. M. J. ; Sharpless , K. B. ; Fokin , V. V. Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(I)-catalyzed ligation of azides and alkynes . Angew. Chem. Int. Ed. 2004 , 43 , 3928 – 3932 ; (b) Helms , B. ; Mynar , J. L. ; Hawker , C. J. ; Frechet , J. M. J. Dendronized linear polymers via “click chemistry.” J. Am. Chem. Soc. 2004 , 126 , 15020 – 15021 ; (c) Scheel , A. ; Komber , H. ; Voit , B. Novel hyperbranched poly([1,2,3]-triazole)s derived from AB2 monomers by a 1,3-dipolar cycloaddition . Macromol. Rapid Commun. 2004 , 25 , 1175 – 1180 ; (d) Parent , M. ; Mongin , O. ; Kamada , K. ; Katan , C. ; Blanchard-Desce , M. New chromophores from click chemistry for two-photon absorption and tuneable photoluminescence . Chem. Commun. 2005 , 2029 – 2031 ; (e) van Steenis , D. J. V. C. ; David , O. R. P. ; van Strijdonck , G. P. F. ; van Maarseveen , J. H. ; Reek , J. N. H. Click chemistry as an efficient synthetic tool for the preparation of novel conjugated polymers . Chem. Commun. 2005 , 4333 – 4335 .
  • (a) Löber , S. ; Rodriguez-Loaiza , P. ; Gmeiner , P. Click linker: Efficient and high-yielding synthesis of a new family of SPOS resins by 1,3-dipolar cycloaddition . Org. Lett. 2003 , 5 , 1753 – 1755 ; (b) Harju , K. ; Vahermo , M. ; Mutikainen , I. ; Yli-Kauhaluoma , J. Solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition . J. Comb. Chem. 2003 , 5 , 826 – 833 ; (c) Khanetskyy , B. ; Dallinger , D. ; Kappe , C. O. Combining Biginelli multicomponent and click chemistry: Generation of 6-(1,2,3-triazol-1-yl)dihydropyrimidone libraries . J. Comb. Chem. 2004 , 6 , 884 – 892 ; (d) Tornoe , C. W. ; Sanderson , S. J. ; Mottram , J. C. ; Coombs , G. H. ; Meldal , M. Combinatorial library of peptidotriazoles: Identification of [1,2,3]-triazole inhibitors against a recombinant Leishmania mexicana cysteine protease . J. Comb. Chem. 2004 , 6 , 312 – 324 .
  • 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. D. ; Stper , D. ; Yagi , B. H. Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious Gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis . J. Med. Chem. 2004 , 43 , 953 – 970 .
  • Wamhoff , H. Comprehensive Heterocyclic Chemistry ; Pergamon Press : Oxford , 1984 .
  • Buckle , D. R. ; Rockell , C. J. M. ; Smith , H. ; Spicer , B. A. Studies on 1,2,3-triazoles, 13: (Piperazinylalkoxy)-[1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-ones with combined H1-antihistamine and mast cell stabilizing properties . J. Med. Chem. 1986 , 29 , 2262 – 2267 .
  • Alvarez , R. ; Velazquez , S. ; San-Felix , A. ; Aquaro , S. ; De Clercq , E. ; Perno , C. F. ; Karlsson , A. ; Balzarini , J. ; Camarasa , M. J. 1,2,3-Triazole-[2,5-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3′-spiro-5″-(4″-amino-1″,2″-oxathiole 2″,2″-dioxide) (TSAO) analogs: Synthesis and anti-HIV-1 activity . J. Med. Chem. 1994 , 37 , 4185 – 4194 .
  • Davis , F. A. ; Lal , G. S. ; Wei , J. Stereo- and regioselective formation of silyl enol ethers via oxidation of vinyl anions . Tetrahedron Lett. 1988 , 29 , 4269 – 4272 .
  • (a) Tsuji , J. Palladium Reagent and Catalysts: Innovations in Organic Synthesis ; Wiley Press : Chichester , 1995 ; (b) Diederich , F. ; Stang , P. J. Metal-Catalyzed Cross-Coupling Reactions ; Wiley-VCH Press : Weinheim , 1998 .
  • Kuang , C. ; Yang , Q. ; Senboku , H. ; Tokuda , M. Stereoselective synthesis of (E)-β-arylvinyl bromides by microwave-induced Hunsdiecker-type reaction . Synthesis 2005 , 8 , 1319 – 1325 .
  • For reviews, see (a) Dömling , A. Recent developments in isocyanide-based multicomponent reactions in applied chemistry. Chem. Rev. 2006, 106, 17–89; (b) Ramón , D. J. ; Yus , M. Asymmetric multicomponent reactions (AMCRs): The new frontier. Angew. Chem., Int. Ed. 2005, 44, 1602–1634.
  • McNulty , J. ; Steere , J. A. ; Wolf , S. The ultrasound-promoted Knoevenagel condensation of aromatic aldehydes . Tetrahedron Lett. 1998 , 39 , 8013 – 8016 .
  • Rao , K. A. N. ; Venkataraman , P. R. Isomeric triazocinnamic acids and related compounds . J. Indian Chem. Soc. 1938 , 15 , 194 – 204 .

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