Literature DB >> 21800069

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.

Mosadegh Keshavarz1, Rashid Badri.   

Abstract

A facile and green synthesis of 1,4-disubstituted-1H-1,2,3-triazoles is reported. The reaction of α-azido ketones and terminal alkynes in the presence of [CuSO(4) (H(2)O)(5)/sodium ascorbate] in a mixture of H(2)O/polyethylene glycol 400 as solvent afforded the corresponding 1,4-disubstituted triazoles at ambient temperature with short reaction times and at high yields. The corresponding α-azido ketones were directly prepared in situ from various substituted styrenes using the oxidant cerium ammonium nitrate and sodium azide in oxygen-saturated methanol.

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Year:  2011        PMID: 21800069     DOI: 10.1007/s11030-011-9327-0

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  11 in total

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Authors:  Hartmuth C. Kolb; M. G. Finn; K. Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2001-06-01       Impact factor: 15.336

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Authors:  Vsevolod V Rostovtsev; Luke G Green; Valery V Fokin; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2002-07-15       Impact factor: 15.336

Review 3.  1,3-dipolar cycloadditions of azides and alkynes: a universal ligation tool in polymer and materials science.

Authors:  Jean-François Lutz
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 4.  Click chemistry and medicinal chemistry: a case of "cyclo-addiction".

Authors:  A D Moorhouse; J E Moses
Journal:  ChemMedChem       Date:  2008-05       Impact factor: 3.466

Review 5.  Click chemistry, a powerful tool for pharmaceutical sciences.

Authors:  Christopher D Hein; Xin-Ming Liu; Dong Wang
Journal:  Pharm Res       Date:  2008-05-29       Impact factor: 4.200

6.  A simple and rapid protocol for the synthesis of phenacyl derivatives using macroporous polymer-supported reagents.

Authors:  Ali R Kiasat; Soheil Sayyahi
Journal:  Mol Divers       Date:  2009-09-11       Impact factor: 2.943

7.  A versatile new monomer family: functionalized 4-vinyl-1,2,3-triazoles via click chemistry.

Authors:  Raymond J Thibault; Kenichi Takizawa; Peter Lowenheilm; Brett Helms; Justin L Mynar; Jean M J Fréchet; Craig J Hawker
Journal:  J Am Chem Soc       Date:  2006-09-20       Impact factor: 15.419

8.  Targeting telomerase and telomeres: a click chemistry approach towards highly selective G-quadruplex ligands.

Authors:  Adam D Moorhouse; Shozeb Haider; Mekala Gunaratnam; Deeksha Munnur; Stephen Neidle; John E Moses
Journal:  Mol Biosyst       Date:  2008-04-08

9.  [Hydroxy(tosyloxy)iodo]benzene mediated alpha-azidation of ketones.

Authors:  Om Prakash; Kamaljeet Pannu; Richa Prakash; Anita Batra
Journal:  Molecules       Date:  2006-07-14       Impact factor: 4.411

Review 10.  The growing applications of click chemistry.

Authors:  John E Moses; Adam D Moorhouse
Journal:  Chem Soc Rev       Date:  2007-05-03       Impact factor: 54.564

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  1 in total

1.  Macroporous polymer supported azide and nanocopper (I): efficient and reusable reagent and catalyst for multicomponent click synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from benzyl halides.

Authors:  Mosadegh Keshavarz; Nasir Iravani; Abdolmohammad Ghaedi; Amanollah Zarei Ahmady; Masoumeh Vafaei-Nezhad; Sara Karimi
Journal:  Springerplus       Date:  2013-02-23
  1 in total

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