A copper(<scp>ii</scp>)–thioamide combination as a robust heterogeneous catalytic system for green synthesis of 1,4-disubstituted-1,2,3-triazoles under click conditions

Mirjafary, Zohreh; Ahmadi, Leila; Moradi, Masomeh; Saeidian, Hamid

doi:10.1039/c5ra16581d

Cited by 29 publications

(11 citation statements)

References 34 publications

(39 reference statements)

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“…On the other hand, Cu(II) species without deliberate addition of a reducing agent for CuAAC reactions have also been investigated. The mechanistic studies indicated that the real catalytic Cu(I) species were generated in a short induction period via reducing Cu(II) salts by alcoholic solvents [127], sodium azide [46,128], or thiobenzanilide [129] especially in the three-component 1,3-dipolar cycloaddition for 1,4-disubstituted 1,2,3-triazoles synthesis. For instance, the recently reported 2-pyrrolecarbaldiminato-Cu(II) complexes efficiently catalyzed three-component 1,3-dipolar cycloaddition reaction of benzyl halides and sodium azide with terminal alkynes in water at r.t., leading to the synthesis of several regioselective 1,4-disubstituted 1,2,3-triazoles in 55-97% yield [130].…”

Section: Cuaacmentioning

confidence: 99%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

286

162

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Highlights-The review is focused on the mechanistic aspects and recent trends (since 2012) of the metal-catalyzed azide-alkyne cycloaddition (MAAC) so-called "click" reactions with catalysts based on various metals (Cu, Ru, Ag, Au, Ir, Ni, Zn, Ln), although Cu (I) catalysts are still the most used ones.-These MAAC reactions are by far the most common click reactions relevant to the "green chemistry" concept.-Mechanistic investigations are essential to reaction improvements and subsequent applications, and indeed as shown in this review the proposed mechanisms have been multiple during the last decade based on theoretical computations and experimental search of intermediates.-New trends are also presented here often representing both exciting approaches for various applications and new challenges for further mechanistic investigations.

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Section: Cuaacmentioning

confidence: 99%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

286

162

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“…[24][25][26][27] Triazoles are an important class of heterocyclic compounds exhibiting a wide range of biological and medicinal properties. In continuation of our interest in the synthesis of various triazole derivatives, [28][29][30][31][32][33][34][35] in this study, new mesoporous silicacoated magnetic nanoparticles (Fe 3 O 4 @SiO 2 @IDA) have been prepared and applied for the synthesis of various 1,4-disubstituted-1,2,3-triazole derivatives. The hybrid nanocatalyst was synthesized by the sol-gel method from Fe 3 O 4 , tetraethoxysilane (TEOS) and 3-chloropropyl triethoxysilane (CPTES), and iminodiacetic acid (IDA) as precursors.…”

Section: Introductionmentioning

confidence: 99%

Highly efficient synthesis of silica‐coated magnetic nanoparticles modified with iminodiacetic acid applied to synthesis of 1,2,3‐triazoles

Godarzbod

Mirjafary

Saeidian

et al. 2020

Applied Organom Chemis

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Great efforts have been made to discover new catalysts to facilitate synthesis of organic fine chemicals. In this research, a new silica-coated magnetic nanoparticles functionalized by iminodiacetic acid (Fe 3 O 4 @SiO 2 @IDA) was prepared by the sol-gel method. The structure of nanoparticles was fully characterized by using X-ray diffraction, scanning electron microscopy, energydispersive X-ray spectroscopy, Fourier transform infrared spectroscopy, and thermogravimetry analysis. The results revealed that the nanoparticles have spherical morphology and an average size of around 40 nm. The analysis also illustrated that the copper nanoparticles had been successfully loaded on the nitrogen-rich carbon support with a uniform distribution. The inductively coupled plasma analysis showed that about 0.22 mmol g −1 of Cu was loaded on the Fe 3 O 4 @SiO 2 @IDA support. Application of Fe 3 O 4 @SiO 2 @IDA-Cu as a magnetically recyclable nanocatalyst for synthesis of 1,4-disubstituted-1,2,3-triazole derivatives through an azide-alkyne [3 + 2] cycloaddition reaction was also investigated. Mild reaction conditions, excellent yields (65-90%), environment-friendly synthesis, and easily prepared starting materials are the key features of the present method. The catalyst is easily removed from the reaction media using an external magnetic field and can be reused at least five times without any considerable loss of its catalytic activity.

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“…Common drugs such as glibenclamide [13], sultiame [14], and COX-II inhibitors Piroxicam [15], Ampiroxicam [16], and Celecoxib [17] containing a sulfonyl moiety, which displays potential activity across a variety of biological targets. The sulfonamides are organic sulfur compounds which have attracted the attention for their better pharmacological activity [18][19][20]. It is interesting to note that the sulfonamide containing moiety is known to have some biological and pharmaceutical properties, such as, antitumor, antibacterial, thrombin inhibition, and antifungal activities [21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Evaluation of Benzenesulfonamide Derivatives

Pansare¹,

Shelke²

2020

Heterocycles - Synthesis and Biological Activities

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A highly efficient protocol was developed for the synthesis of 3-(indoline-1carbonyl)-N-(substituted) benzene sulfonamide analogs with excellent yields. The new 3-(indoline-1-carbonyl)-N-(substituted) benzene sulfonamide derivatives (4a-g and 5a-g) were evaluated in vitro anticancer activity against a series of different cell lines like A549 (lung cancer cell), HeLa (cervical), MCF-7 (breast cancer cell) and Du-145 (prostate cancer cell) respectively. The results of the anticancer activity data revealed that most of the tested compounds showed IC 50 values from 1.98 to 9.12 μM in different cell lines. Compounds 4b, 4d, 5d, and 5g were the most potent, with IC 50 values ranging from 1.98 to 2.72 μM in different cell lines.

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A copper(ii)–thioamide combination as a robust heterogeneous catalytic system for green synthesis of 1,4-disubstituted-1,2,3-triazoles under click conditions

Abstract: One-pot synthesis of 1,4-disubstituted-1,2,3-triazoles 3 using copper(ii)–thioamide combination was reported.

Cited by 29 publications

References 34 publications

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Highly efficient synthesis of silica‐coated magnetic nanoparticles modified with iminodiacetic acid applied to synthesis of 1,2,3‐triazoles

Synthesis and Anticancer Evaluation of Benzenesulfonamide Derivatives

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