Multicomponent Synthesis and Evaluation of New 1,2,3-Triazole Derivatives of Dihydropyrimidinones as Acidic Corrosion Inhibitors for Steel

被引：40

作者：

Gonzalez-Olvera, Rodrigo ^{[1
]}

Roman-Rodriguez, Viridiana ^{[1
]}

Negron-Silva, Guillermo E. ^{[1
]}

Espinoza-Vazquez, Araceli ^{[2
]}

Javier Rodriguez-Gomez, Francisco ^{[2
]}

Santillan, Rosa ^{[3
]}

机构：

[1] Univ Autonoma Metropolitana Azcapotzalco, Dept Ciencias Basicas, Av San Pablo 180, Ciudad De Mexico 02200, DF, Mexico

[2] Univ Nacl Autonoma Mexico, Fac Quim, Dept Ingn Met, CU, Ciudad De Mexico 04510, DF, Mexico

[3] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Apartado Postal 14-740, Ciudad De Mexico 07000, DF, Mexico

来源：

MOLECULES | 2016年 / 21卷 / 02期

关键词：

multicomponent synthesis; dihydropyrimidinone; 1; 2; 3-triazole; corrosion inhibitor; steel; ONE-POT SYNTHESIS; MILD-STEEL; CLICK CHEMISTRY; TRIAZOLE; DISCOVERY; URACIL;

D O I：

10.3390/molecules21020250

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An efficient one-pot synthesis of 1,2,3-triazole derivatives of dihydropyrimidinones has been developed using two multicomponent reactions. The aldehyde-1,2,3-triazoles were obtained in good yields from in situ-generated organic azides and O-propargylbenzaldehyde. The target heterocycles were synthesized through the Biginelli reaction in which the aldehyde-1,2,3-triazoles reacted with ethyl acetoacetate and urea in the presence of Ce(OTf)(3) as the catalyst. The corrosion inhibition of steel grade API 5 L X52 in 1 M HCl by the synthesized compounds was investigated using the electrochemical impedance spectroscopy technique. The measurements revealed that these heterocycles are promising candidates to inhibit acidic corrosion of steel.

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页数：13

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[1]

AM. PETROL. INST, 2004, AM PETR I STAND, P8

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Fokin, VV ;

Van der Eycken, E .

ORGANIC LETTERS, 2004, 6 (23) :4223-4225

[3] A novel green synthesis of α/β-amino acid functionalized pyrimidinone peptidomimetics using triazole ligation through click-multi-component reactions [J].

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[4] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].

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[5] The inhibition effect of some pyrimidine derivatives on austenitic stainless steel in acidic media [J].

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[9] Identification of diverse 1,2,3-triazole-connected benzyl glycoside-serine/threonine conjugates as potent corrosion inhibitors for mild steel in HCl [J].

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