Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2014; 46(09): 1217-1223
DOI: 10.1055/s-0033-1340863
DOI: 10.1055/s-0033-1340863
paper
One-Pot Three-Component Synthesis of New Mono- and Bis-1,2,3-triazole Derivatives of 2-Benzimidazolethiol with a Promising Inhibitory Activity against Acidic Corrosion of Steel
Further Information
Publication History
Received: 30 December 2013
Accepted after revision: 04 February 2014
Publication Date:
25 February 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201409/lookinside/thumbnails/10.1055-s-0033-1340863-1.jpg)
Abstract
A series of new mono- and bis-1,2,3-triazole derivatives of 2-benzimidazolethiol were synthesized by three-component copper(I)-catalyzed 1,3-dipolar cycloaddition. The desired heterocycles were obtained in good yields and fully characterized. The corrosion inhibition efficiency of new heterocyclic compounds was investigated on steel grade API 5L X52 in 1 M HCl using electrochemical impedance spectroscopy. The results revealed that these new organic compounds show promising inhibition properties for the corrosion of steel in acidic media.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Ganesh A. Int. J. Chem. Sci. 2013; 11: 573
- 1b Agalave SG, Maujan SR, Pore VS. Chem. Asian J. 2011; 6: 2696
-
2a Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 2b Tornøe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
- 3a Bock VD, Hiemstra H, van Maarseveen JH. Eur. J. Org. Chem. 2006; 51
-
3b Meldal M, Tornøe CW. Chem. Rev. 2008; 108: 2952
- 3c Gramlich PM. E, Wirges CT, Manetto A, Carell T. Angew. Chem. Int. Ed. 2008; 47: 8350
- 3d Amblard F, Cho JH, Schinazi RF. Chem. Rev. 2009; 109: 4207
-
3e Hein JE, Fokin VV. Chem. Soc. Rev. 2010; 39: 1302
- 3f Struthers H, Mindt TL, Schibli R. Dalton Trans. 2010; 39: 675
- 3g Lallana E, Riguera R, Fernandez-Mejia E. Angew. Chem. Int. Ed. 2011; 50: 8794
- 3h Pedersen DS, Abell A. Eur. J. Org. Chem. 2011; 2399
- 3i Efthymiou T, Gong W, Desaulniers J.-P. Molecules 2012; 17: 12665
- 3j He X.-P, Xie J, Tang Y, Li J, Chen G.-R. Curr. Med. Chem. 2012; 19: 2399
- 3k Pasini D. Molecules 2013; 18: 9512
- 3l Avti PV, Maysinger D, Kakkar A. Molecules 2013; 18: 9531
- 3m Li H, Aneja R, Chaiken I. Molecules 2013; 18: 9797
- 3n Ahmad Fuaad AA. H, Azmi F, Skwarczynski M, Toth I. Molecules 2013; 18: 13148
- 4a González-Olvera R, Espinoza-Vázquez A, Negrón-Silva GE, Palomar-Pardavé ME, Romero-Romo MA, Santillan R. Molecules 2013; 18: 15064
- 4b Deng Q, He X.-P, Shi H.-W, Chen B.-Q, Liu G, Tang Y, Long Y.-T, Chen GR, Chen K. Ind. Eng. Chem. Res. 2012; 51: 7160
- 4c Deng Q, Ding N.-N, Wei X.-L, Cai L, He X.-P, Long Y.-T, Chen G.-R, Chen K. Corros. Sci. 2012; 64: 64
- 4d Deng Q, Shi H.-W, Ding N.-N, Chen B.-Q, He X.-P, Liu G, Tang Y, Long Y.-T, Chen G.-R. Corros. Sci. 2012; 57: 220
- 4e Zhang H.-L, He X.-P, Deng Q, Long Y.-T, Chen G.-R, Chen K. Carbohydr. Res. 2012; 354: 32
- 4f Babić-Samardžija K, Hacherman N. J. Solid State Electrochem. 2005; 9: 483
- 4g Abdennabi AM. S, Abdulhadi AI, Abu-Orani ST, Saricimen H. Corros. Sci. 1996; 38: 1791
- 5a Olvera-Martinez ME, Mendoza-Flores J, Rodriguez-Gomez FJ, Palomar-Pardave ME, Genesca J. Mater. Corros. 2013; 64: 522
- 5b Benabdellah M, Tounsi A, Khaled KF, Hammouti B. Arabian J. Chem. 2011; 4: 17 ; Chem. Abstr. 2010, 154, 289472
- 5c Mahdavian M, Ashhari S. Electrochim. Acta 2010; 55: 1720
- 5d Forsal I, Ebn Touhami M, Mernari B, El Hajri J, Filali Baba M. Port. Electrochim. Acta 2010; 28: 203
- 5e Aljourani J, Raeissi K, Golozar MA. Corros. Sci. 2009; 51: 1836
- 5f Popova A, Christov M, Raicheva S, Sokolova E. Corros. Sci. 2004; 46: 1333
- 5g Popova A, Sokolova E, Raicheva S, Christov M. Corros. Sci. 2003; 45: 33
- 6a Shah K, Chhabra S, Shrivastava SK, Mishra P. Med. Chem. Res. 2013; 22: 5077
- 6b Narasimhan B, Sharma D, Kumar P. Med. Chem. Res. 2012; 21: 269
- 6c Bansal Y, Silakari O. Bioorg. Med. Chem. 2012; 20: 6208
- 6d Chawla A, Kaur R, Goyal A. J. Chem. Pharm. Res. 2011; 3: 925
- 7 Cruz-Gonzalez DY, González-Olvera R, Angeles-Beltrán D, Negrón-Silva GE, Santillan R. Synthesis 2013; 45: 3281
- 8a Cruz-Gonzalez DY, Negrón-Silva G, Angeles-Beltrán D, Palomar-Pardavé M, Romero-Romo M, Uruchurtu-Chavarín J. ECS Trans. 2011; 36: 197
- 8b Espinoza A, Negrón G, Palomar-Pardavé M, Romero-Romo MA, Rodríguez-Torres I, Herrera-Hernández H. ECS Trans. 2009; 20: 543
- 8c Morales-Gil P, Negrón-Silva G, Romero-Romo M, Ángeles-Chávez C, Palomar-Pardavé M. Electrochim. Acta 2004; 49: 4733
- 9a Negrón-Silva GE, González-Olvera R, Angeles-Beltrán D, Maldonado-Carmona N, Espinoza-Vázquez A, Palomar-Pardavé ME, Romero-Romo MA, Santillan R. Molecules 2013; 18: 4613
- 9b Mendoza-Espinosa D, Negrón-Silva GE, Lomas-Romero L, Gutiérrez-Carrillo A, Soto-Castro D. Synthesis 2013; 45: 2431
- 10a Hwang S, Bae H, Kim S, Kim S. Tetrahedron 2012; 68: 1460
- 10b Lewis WG, Magallon FG, Fokin VV, Finn MG. J. Am. Chem. Soc. 2004; 126: 9152
- 11 Creutz C. Inorg. Chem. 1981; 20: 4449
- 12 Creary X, Anderson A, Brophy C, Crowell F, Funk Z. J. Org. Chem. 2012; 77: 8756
- 13a Yadav M, Behera D, Kumar S, Sinha RR. Ind. Eng. Chem. Res. 2013; 52: 6318
- 13b Ouici HB, Benali O, Harek Y, Larabi L, Hammouti B, Guendouzi A. Res. Chem. Intermed. 2013; 39: 2777
- 13c Ansari KR, Yadav DK, Ebenso EE, Quraishi MA. Int. J. Electrochem. Sci. 2012; 7: 4780
- 13d Kumar MS, Kumar SL, Sreekanth A. Ind. Eng. Chem. Res. 2012; 51: 5408
- 13e Nataraja SE, Venkatesha TV, Manjunatha K, Poojary B, Pavithra MK, Tandon HC. Corros. Sci. 2011; 53: 2651
- 13f Khadom AA, Musa AY, Kadhum AA. H, Mohamed AB, Takriff MS. Port. Electrochim. Acta 2010; 28: 221
- 13g Álvarez-Bustamante R, Negrón-Silva G, Abreu-Quijano M, Herrera-Hernández H, Romero-Romo M, Cuán A, Palomar-Pardavé M. Electrochim. Acta 2009; 54: 5393
- 13h Hassan HH, Abdelghani E, Amin MA. Electrochim. Acta 2007; 52: 6359
- 13i Quraishi MA, Sharma HK. Mater. Chem. Phys. 2002; 78: 18