Multicomponent Click Synthesis of New 1,2,3-Triazole Derivatives of Pyrimidine Nucleobases: Promising Acidic Corrosion Inhibitors for Steel

被引：53

作者：

Gonzalez-Olvera, Rodrigo ^{[1
]}

Espinoza-Vazquez, Araceli ^{[1
,2
]}

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

Palomar-Pardave, Manuel E. ^{[2
]}

Romero-Romo, Mario A. ^{[2
]}

Santillan, Rosa ^{[3
]}

机构：

[1] Univ Autonoma Metropolitana, Dept Ciencias Basicas, Mexico City 02200, DF, Mexico

[2] Univ Autonoma Metropolitana, Dept Mat, Mexico City 02200, DF, Mexico

[3] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico

来源：

MOLECULES | 2013年 / 18卷 / 12期

关键词：

nucleobases; multicomponent reaction; 1,2,3-triazoles; acidic corrosion; steel; MILD-STEEL; 1,3-DIPOLAR CYCLOADDITION; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; NUCLEOSIDE DERIVATIVES; NUCLEOTIDE ANALOGS; CHEMISTRY APPROACH; TERMINAL ALKYNES; CARBON-STEEL; HCL SOLUTION; AZIDE;

D O I：

10.3390/molecules181215064

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：

A series of new mono-1,2,3-triazole derivatives of pyrimidine nucleobases were synthesized by one-pot copper(I)-catalyzed 1,3-dipolar cycloaddition reactions between N-1-propargyluracil and thymine, sodium azide and several benzyl halides. The desired heterocyclic compounds were obtained in good yields and characterized by NMR, IR, and high resolution mass spectrometry. These compounds were investigated as corrosion inhibitors for steel in 1 M HCl solution, using electrochemical impedance spectroscopy (EIS) technique. The results indicate that these heterocyclic compounds are promising acidic corrosion inhibitors for steel.

引用

页码：15064 / 15079

页数：16

共 57 条

[1] Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].

Agalave, Sandip G. ;

Maujan, Suleman R. ;

Pore, Vandana S. .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2696-2718

[2]

Alaoui L.M., 2011, PHARM CHEM J+, V3, P353

[3] Cu(I)-Catalyzed Huisgen Azide-Alkyne 1,3-Dipolar Cycloaddition Reaction in Nucleoside, Nucleotide, and Oligonucleotide Chemistry [J].

Amblard, Franck ;

Cho, Jong Hyun ;

Schinazi, Raymond F. .

CHEMICAL REVIEWS, 2009, 109 (09) :4207-4220

[4]

Ansari KR, 2012, INT J ELECTROCHEM SC, V7, P4780

[5] A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction [J].

Appukkuttan, P ;

Dehaen, W ;

Fokin, VV ;

Van der Eycken, E .

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

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

Bock, VD ;

Hiemstra, H ;

van Maarseveen, JH .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68

[7]

Chandrasekhar S, 2006, TETRAHEDRON LETT, V47, P47, DOI [10.1016/j.tetlet.2005.10.129, 10.1016/j.tetlet.2006.03.037]

[8] Nucleosides and oligonucleotides containing 1,2,3-triazole residues with nucleobase tethers: Synthesis via the azide-alkyne 'click' reaction [J].

Chittepu, Padmaja ;

Sirivolu, Venkata Ramana ;

Seela, Frank .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (18) :8427-8439

[9] Method for Assigning Structure of 1,2,3-Triazoles [J].

Creary, Xavier ;

Anderson, Andrew ;

Brophy, Carl ;

Crowell, Frances ;

Funk, Zachary .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (19) :8756-8761

[10]

Cruz-Gonzalez D.Y., 2011, ECS T, V36, P179

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