A facile and one pot synthesis of 1, 4-disubstituted- 1H-1, 2, 3-triazoles from terminal alkynes and phenacyl azides prepared from styrenes by CAN oxidant and sodium azide

Molecular Diversity

Volumn 15, Issue 4, 2011, Pages 957-962

  Keshavarz, Mosadegh ^a   Badri, Rashid ^a  

^a SHAHID CHAMRAN UNIVERSITY OF AHVAZ   (Iran)

Author keywords

Click chemistry; Regioselective; Sodium azide; Styrene; Triazole

Indexed keywords

1,2,3 TRIAZINE DERIVATIVE; ALKYNE DERIVATIVE; ASCORBIC ACID; AZIDE; CERIUM AMMONIUM NITRATE; KETONE DERIVATIVE; MACROGOL; METHANOL; OXIDIZING AGENT; SODIUM AZIDE; STYRENE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CLICK CHEMISTRY; CONTROLLED STUDY; CYCLIZATION; CYCLOADDITION; FACILE SYNTHESIS; ONE POT SYNTHESIS; OXYGEN SATURATION; PRIORITY JOURNAL; QUANTUM YIELD; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

ALKYNES; CERIUM; CHEMISTRY TECHNIQUES, SYNTHETIC; CLICK CHEMISTRY; NITRATES; OXIDANTS; SODIUM AZIDE; STYRENE; TRIAZOLES;

EID: 84855230919     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-011-9327-0     Document Type: Article

References (27)

1. PadwaA, PearsonWH(2003) Synthetic applications of 1, 3-dipolar cycloaddition chemistry toward heterocycles and natural products, vol. 59. chap 9.Wiley-Interscience, NewYork, pp 639-644. doi:10.1002/0471221902.ch9
2. Lwowsky W (1984) 1, 3-dipolar cycloaddition chemistry, vol 1, Chap. 4. Wiley-Interscience, New York 621-627
3. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Astepwise 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) (Pubitemid 34803480)
4. Kolb HC, FinnMG, 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)
5. 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 (Pubitemid 47409277)
6. Binder WH, Sachsenhofer R (2007) 'Click' chemistry in polymer and materials science. Macromol Rapid Commun 28:15-54. doi:10.1002/marc.200600625 (Pubitemid 46192085)
7. 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 (Pubitemid 46959349)
8. Breinbauer R, KohnM (2003) Azide-alkyne coupling: a powerful reaction for bioconjugate chemistry. ChemBioChem 4:1147-1149. doi:10.1002/cbic.200300705 (Pubitemid 37462815)
9. Hein CD, LiuXM, WangD (2008) Click chemistry, a powerful tool for pharmaceutical sciences. Pharm Res 25:2216-2230. doi:10.1007/s11095-008-9616-1
10. 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 (Pubitemid 351706307)
11. Moorhouse AD, Moses JE (2008) Click chemistry and medicinal chemistry: a case of cyclo-addiction. ChemMedChem 3:715-723. doi:10.1002/cmdc.200700334
12. GilMV, ArevaloMJ, Lopez O (2007) Click chemistry-what's in a name? Triazole synthesis and beyond. Synthesis 11:1589-1620. doi:10.1055/s-2007-966071 (Pubitemid 46911512)
13. Moses JE, Moorhouse AD (2007) The growing applications of click chemistry. Chem Soc Rev 36:1249. doi:10.1039/B613014N
14. 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
15. 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 (Pubitemid 44413837)
16. Scriven EFV, TurnbullK (1988) Azides: their preparation and synthetic uses. Chem Rev 88:297. doi:10.1021/cr00084a001
17. Snyder JP, Spangler DP, Behling JR, Rossiter BE (1994) The structure of "R2Cu(CN)Li2" lithium cuprates: lower-order aggregates of gilman reagents and organo lithium compounds. J Org Chem 59:2902-2905. doi:10.1021/jo00089a043
18. 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
19. 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 (Pubitemid 44252741)
20. 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
21. 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
22. 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
23. Marsh FD (1972) Cyanogen azide. J Org Chem 37:2966. doi:10. 1021/jo00984a012
24. 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
25. AlexandruG, 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 (Pubitemid 44663575)
26. 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 (Pubitemid 40524262)
27. 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