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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 1
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Original Articles

Application of Hantzsch Dihydropyridine in Copper-Catalyzed [3 + 2] Cycloaddition of Terminal Alkynes with Azides

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Pages 68-75 | Received 26 Dec 2012, Published online: 11 Oct 2013

REFERENCES

  • 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 .
  • (a) Zhang , L. ; Chen , X. G. ; Xue , P. ; Sung , H. H. Y. ; Williams , I. D. ; Sharpless , K. B. ; Fokin , V. V. ; Jia , G. C. Ruthenium-catalyzed cycloaddition of alkynes and organic azides . J. Am. Chem. Soc. 2005 , 127 , 15998 – 15999 ; (b) McNulty , J. ; Keskar , K. ; Vemula , R. The first well-defined silver(I)-complex-catalyzed cycloaddition of azides onto terminal alkynes at room temperature . Chem. Eur. J. 2011 , 17 , 14727 – 14730 .
  • (a) Kamata , K. ; Nakagawa , Y. ; Yamaguchi , K. ; Mizuno , N. 1,3-Dipolar cycloaddition of organic azides to alkynes by a dicopper-substituted silicotungstate . J. Am. Chem. Soc. 2008 , 130 , 15304 – 15310 ; (b) Alonso , F. ; Moglie , Y. ; Radivoy , G. ; Yus , M. Copper-catalysed multicomponent click synthesis of 5-alkynyl 1,2,3-triazoles under ambient conditions . Synlett 2012 , 23 , 2179 – 2182 .
  • Liang , L.-Y. ; Astruc , D. The copper(I)-catalyzed alkyne–azide cycloaddition (CuAAC) “click” reaction and its applications: An overview . Coord. Chem. Rev. 2011 , 255 , 2933 – 2945 .
  • Kolb , H. C. ; Sharpless , K. B. The growing impact of click chemistry on drug discovery . Drug Discov. Today 2003 , 8 , 1128 – 1137 .
  • 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 .
  • Meldal , M. ; Tornøe , C. W. Cu-catalyzed azide–alkyne cycloaddition . Chem. Rev. 2008 , 108 , 2952 – 3015 , and references therein .
  • Shao , C.-W. ; Cheng , G.-L. ; Su , D.-Y. ; Xu , J.-M. ; Wang , X.-Y. ; Hu , Y.-F. Copper(І) acetate: A structurally simple but highly efficient dinuclear catalyst for copper-catalyzed azide–alkyne cycloaddition . Adv. Synth. Catal. 2010 , 352 , 1587 – 1592 .
  • (a) Bock , V. D. ; Hiemstra , H. ; van Maarseveen , J. H. CuI-catalyzed alkyne–azide “click” cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem. 2006, 1, 51–68; (b) Buckley , B. R. ; Dann , S. E. ; Harris , D. P. ; Heaney , H. ; Stubbs , E. C. Alkynylcopper(I) polymers and their use in a mechanistic study of alkyne–azide click reactions. Chem. Commun. 2010, 46, 2274–2276.
  • Zhang , X.-J. ; Li , H.-Y. ; You , L.-F. ; Tang , Y. ; Hsung , R. P. Copper salt–catalyzed azide–[3 + 2] cycloadditions of ynamides and bis-ynamides . Adv. Synth. Catal. 2006 , 348 , 2437 – 2442 .
  • Candelon , N. ; Lastecoueres , D. ; Diallo , A. K. ; Aranzaes , J. R. ; Astruc , D. ; Vincent , J.-M. A highly active and reusable copper(I)-tren catalyst for the ‘‘click'’ 1,3-dipolar cycloaddition of azides and alkynes . Chem. Commun. 2008 , 741 – 743 .
  • (a) Lipshutz , B. H. ; Taft , B. R. Heterogeneous copper-in-charcoal-catalyzed click chemistry . Angew. Chem., Int. Ed. 2006 , 45 , 8235 – 8238 ; (b) Chassaing , S. ; Kumarraja , M. ; Sido , A. S. S. ; Pale , P. ; Sommer , J. Click chemistry in CuI-zeolites: The Huisgen [3 + 2]-cycloaddition . Org. Lett. 2007 , 9 , 883 – 886 .
  • (a) Sharghi , H. ; Khalifeh , R. ; Doroodmand , M. M. Copper nanoparticles on charcoal for multicomponent catalytic synthesis of 1,2,3-triazole derivatives from benzyl halides or alkyl halides, terminal alkynes, and sodium azide in water as a “green” solvent . Adv. Synth. Catal. 2009 , 351 , 207 – 218 ; (b) Sarkar , A. ; Mukherjee , T. ; Kapoor , S. PVP-stabilized copper nanoparticles: A reusable catalyst for “click” reaction between terminal alkynes and azides in nonaqueous solvents . J. Phys. Chem. C 2008 , 112 , 3334 – 3340 .
  • (a) Campbell-Verduyn , L. S. ; Mirfeizi , L. ; Dierckx , R. A. ; Elsinga , P. H. ; Feringa , B. L. Phosphoramidite accelerated copper(I)-catalyzed [3 + 2] cycloadditions of azides and alkynes . Chem. Commun. 2009 , 45 , 2139 – 2141 ; (b) Díez-González , S. ; Nolan , S. P. [(NHC)2Cu]X complexes as efficient catalysts for azide–alkyne click chemistry at low catalyst loadings . Angew. Chem., Int. Ed. 2008 , 47 , 8881 – 8884 .
  • Kuang , G.-C. ; Michaels , H. A. ; Simmons , J. T. ; Clark , R. J. ; Zhu , L. Chelation-assisted, copper(II)-acetate-accelerated azide–alkyne cycloaddition . J. Org. Chem. 2010 , 75 , 6540 – 6548 .
  • Saini , A. ; Kumar , S. ; Sandhu , J. S. New strategy for the oxidation of Hantzsch 1,4-dihydropyridines and dihydropyrido[2,3-d]pyrimidines catalyzed by DMSO under aerobic conditions . Synth. Commun. 2007 , 37 , 2317 – 2324 .
  • (a) Murata , M. ; Kobayashi , M. ; Kawanishi , S. Nonenzymatic reduction of nitro derivative of a heterocyclic amine IQ by NADH and Cu(II) leads to oxidative DNA damage . Biochemistry 1999 , 38 , 7624 – 7629 ; (b) Ouellet , S. G. ; Walji , A. M. ; MacMillan , D. W. C. Enantioselective organocatalytic transfer hydrogenation reactions using Hantzsch esters . Acc. Chem. Res. 2007 , 40 , 1327 – 1339 .
  • Rowan , K. R. ; Holt , E. M. 3,5-Dimethoxycarbonyl-2,6-dimethyl-4-(2-nitroso-phenyl)pyridine and dichlorobis[3,5-dimethoxycarbonyl-2,6-dimethyl-4-(2-nitrophenyl)pyridine]copper(II) . Acta Cryst. 1995 , C51 , 2554 – 2559 .

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