Literature DB >> 24866914

An efficient catalytic system based on 7,8-dihydroxy-4-methylcoumarin and copper(II) for the click synthesis of diverse 1,4-disubstituted-1,2,3-triazoles under green conditions.

Hashem Sharghi1, Pezhman Shiri, Mahdi Aberi.   

Abstract

In this work, the combination of 7,8-dihydroxy-4-methyl coumarin (DHMC) as a novel bidentate O,O-chelating agent and copper(II) acetate monohydrate (2:1 molar ratio) has been found to form an efficient catalytic system. This catalyst provided good to excellent yields in the multi-component click synthesis of 1,4-disubstituted-1,2,3-triazoles by using various structurally diverse organic halides, different non-activated terminal alkynes, and sodium azide. This catalytic system eliminates the need for the isolation of the hazardous azide intermediates which are generated in situ. The reaction is carried out in aqueous phase at room temperature and it can be accelerated by sonication or by increasing the reaction temperature. Moreover, the reaction can be performed in large scale. It is noteworthy that DHMC is commercially available and that it can be easily synthesized with low cost materials.

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Year:  2014        PMID: 24866914     DOI: 10.1007/s11030-014-9527-5

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


  25 in total

1.  Ultrasonic-assisted synthesis of chrysin derivatives linked with 1,2,3-triazoles by 1,3-dipolar cycloaddition reaction.

Authors:  Yuqin Jiang; Xiaolan Chen; Lingbo Qu; Junliang Wang; Jinwei Yuan; Senshen Chen; Xu Li; Chen Qu
Journal:  Ultrason Sonochem       Date:  2010-09-29       Impact factor: 7.491

2.  Structure, photophysics, electrochemistry, DFT calculation, and in-vitro antioxidant activity of coumarin Schiff base complexes of Group 6 metal carbonyls.

Authors:  Papia Datta; Ambika Prasad Mukhopadhyay; Prasenjit Manna; Edward R T Tiekink; Parames Chandra Sil; Chittaranjan Sinha
Journal:  J Inorg Biochem       Date:  2010-05-15       Impact factor: 4.155

3.  Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates.

Authors:  Fahmi Himo; Timothy Lovell; Robert Hilgraf; Vsevolod V Rostovtsev; Louis Noodleman; K Barry Sharpless; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2005-01-12       Impact factor: 15.419

4.  Alkenes as azido precursors for the one-pot synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon.

Authors:  Francisco Alonso; Yanina Moglie; Gabriel Radivoy; Miguel Yus
Journal:  J Org Chem       Date:  2013-05-06       Impact factor: 4.354

5.  Phosphoramidite accelerated copper(i)-catalyzed [3 + 2] cycloadditions of azides and alkynes.

Authors:  Lachlan S Campbell-Verduyn; Leila Mirfeizi; Rudi A Dierckx; Philip H Elsinga; Ben L Feringa
Journal:  Chem Commun (Camb)       Date:  2009-03-19       Impact factor: 6.222

6.  Amphiphilic self-assembled polymeric copper catalyst to parts per million levels: click chemistry.

Authors:  Yoichi M A Yamada; Shaheen M Sarkar; Yasuhiro Uozumi
Journal:  J Am Chem Soc       Date:  2012-05-29       Impact factor: 15.419

7.  Cu(II)-hydrotalcite as an efficient heterogeneous catalyst for Huisgen [3+2] cycloaddition.

Authors:  Kayambu Namitharan; Mayilvasagam Kumarraja; Kasi Pitchumani
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

8.  (E)-N-(4-{[1-(Prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]meth-oxy}benzyl-idene)morpholin-4-amine.

Authors:  Mehmet Akkurt; Aliasghar Jarrahpour; Mehdi Mohammadi Chermahini; Pezhman Shiri; Namık Ozdemir
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-02-12

9.  (E)-N-(1,3-Benzodioxol-5-yl)-1-(4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]meth-oxy}phen-yl)methanimine.

Authors:  Mehmet Akkurt; Aliasghar Jarrahpour; Mehdi Mohammadi Chermahini; Pezhman Shiri; Orhan Büyükgüngör
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-09-21

10.  3,4-Dimeth-oxy-N-((E)-4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]meth-oxy}benzyl-idene)aniline.

Authors:  Mehmet Akkurt; Aliasghar Jarrahpour; Hashem Sharghi; Mehdi Mohammadi Chermahini; Pezhman Shiri; Orhan Büyükgüngör
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-06-16
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  2 in total

1.  Supported Cu(II)-Schiff base: novel heterogeneous catalyst with extremely high activity for eco-friendly, one-pot and multi-component C-S bond-forming reaction toward a wide range of thioethers as biologically active cores.

Authors:  Pezhman Shiri; Ali Mohammad Amani; Jasem Aboonajmi
Journal:  Mol Divers       Date:  2021-05-12       Impact factor: 2.943

2.  Solvent-free and room temperature synthesis of 3-arylquinolines from different anilines and styrene oxide in the presence of Al2O3/MeSO3H.

Authors:  Hashem Sharghi; Mahdi Aberi; Mohsen Khataminejad; Pezhman Shiri
Journal:  Beilstein J Org Chem       Date:  2017-09-20       Impact factor: 2.883

  2 in total

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