Phương pháp tổng hợp đơn giản và một bước 1,4-disubstituted-1H-1,2,3-triazoles từ các alkyne đầu và phenacyl azides được chuẩn bị từ styrenes bởi chất oxy hóa CAN và natri azide

Padwa A, Pearson WH (2003) Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products, vol. 59. chap 9. Wiley-Interscience, New York, pp 639–644. doi:10.1002/0471221902.ch9 Lwowsky W (1984) 1,3-dipolar cycloaddition chemistry, vol 1, Chap. 4. Wiley-Interscience, New York, pp 621–627 Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) A stepwise huisgen cycloaddition process: copper(i)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew Chem Int Ed 41: 2596–2599. doi:10.1002/1521-3773(20020715) Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 40: 2004–2021. doi:10.1002/1521-3773(20010601) Nandivada H, Jiang X, Lahann J (2007) Click chemistry: versatility and control in the hands of materials scientists. J Adv Mater 19: 2197–2208. doi:10.1002/adma.200602739 Binder WH, Sachsenhofer R (2007) ‘Click’ chemistry in polymer and materials science. Macromol Rapid Commun 28: 15–54. doi:10.1002/marc.200600625 Lutz JF (2007) 1,3-dipolar cycloadditions of azides and alkynes: a universal ligation tool in polymer and materials. Angew Chem Int Ed 46: 1018–1025. doi:10.1002/anie.200604050 Breinbauer R, Kohn M (2003) Azide–alkyne coupling: a powerful reaction for bioconjugate chemistry. ChemBioChem 4: 1147–1149. doi:10.1002/cbic.200300705 Hein CD, Liu XM, Wang D (2008) Click chemistry, a powerful tool for pharmaceutical sciences. Pharm Res 25: 2216–2230. doi:10.1007/s11095-008-9616-1 Moorhouse AD, Haider S, Gunaratnam M, Munnur D, Neidle S, Moses JE (2008) Targeting telomerase and telomeres: a click chemistry approach towards highly selective G-quadruplex ligands. Mol BioSyst 4: 629–642. doi:10.1039/B801822G Moorhouse AD, Moses JE (2008) Click chemistry and medicinal chemistry: a case of cyclo-addiction. ChemMedChem 3: 715–723. doi:10.1002/cmdc.200700334 Gil MV, Arevalo MJ, Lopez O (2007) Click chemistry—what’s in a name? Triazole synthesis and beyond. Synthesis 11: 1589–1620. doi:10.1055/s-2007-966071 Moses JE, Moorhouse AD (2007) The growing applications of click chemistry. Chem Soc Rev 36: 1249. doi:10.1039/B613014N Bock VD, Hiemstra H, Maarseveen JH (2006) Cu(I)-catalyzed alkyne-azide “click” cycloadditions from a mechanistic and synthetic perspective. Eur J Org Chem 51–68. doi:10.1002/ejoc.200500483 Thibault RJ, Takizawa K, Lowenheilm P, Helms B, Mynar JL, Frechet JMJ, Hawker CJ (2006) A versatile new monomer family: functionalized 4-vinyl-1,2,3-triazoles via click chemistry. J Am Chem Soc 128: 12084. doi:10.1021/ja0648209 Scriven EFV, Turnbull K (1988) Azides: their preparation and synthetic uses. Chem Rev 88: 297. doi:10.1021/cr00084a001 Snyder JP, Spangler DP, Behling JR, Rossiter BE (1994) The structure of “R 2 Cu(CN)Li 2” lithium cuprates: lower-order aggregates of gilman reagents and organo lithium compounds. J Org Chem 59: 2902–2905. doi:10.1021/jo00089a043 Kiasat AR, Sayyahi S (2010) A simple and rapid protocol for the synthesis of phenacyl derivatives using macroporous polymer-supported reagents. Mol Divers 14: 155–158. doi:10.1007/s11030-009-9191-3 Prakash O, Pannu K, Prakash R, Batra A (2006) [Hydroxy(tosyloxy)iodo]benzene mediated α-azidation of ketones. Molecules 11: 523–527. doi:10.3390/11070523 Nair V, Nair LG, George TG, Augustine A (2000) Cerium (IV) ammonium nitrate mediated addition of thiocyanate and azide to styrenes: expeditious routes to phenacyl thiocyanates and phenacyl azides. Tetrahedron 56: 7607–7611. doi:10.1016/s0040-4020(00)00675-x Kumar D et al (2009) A facile and regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles using click chemistry. Tetrahedron Lett 50: 2065–2068. doi:10.1016/j.tetlet.2009.02.107 Kumar D et al (2009) Greener and expeditious synthesis of 1,4-disubstituted 1,2,3-triazoles from terminal acetylenes and in situ generated α-azido ketones. Synlett 3: 399–402. doi:10.1055/s-0028-1087556 Marsh FD (1972) Cyanogen azide. J Org Chem 37: 2966. doi:10.1021/jo00984a012 Priebe H, Braathen GO, Klaeboe P, Neelsen C (1984) Ultrasound synthesis of propagyl azide, azidoacetonitrile and primary allylic azides. Acta Chem Scand Ser B 38: 895 Alexandru G, Erick CY, Joachim H, Willi B, Narasaiah B, Oliver R (2006) A facile strategy to a new fluorous-tagged, immobilized tempo catalyst using a click reaction, and its catalytic activity. Synlett 17: 2767. doi:10.1055/s-2006-950256 Karol K (2005) Efficient one-pot synthesis of 1,2,3-triazoles from benzyl and alkyl halides. Synlett 6: 943. doi:10.1055/s-2005-864809 Kristin O, Edmund AH, Trond VH (2007) One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from terminal acetylenes and in situ generated azides. Tetrahedron Lett 48: 2097. doi:10.1016/j.tetlet.2007.01.130