Synthesis of α‐Aminonitriles and 5‐Substituted 1H‐Tetrazoles Using an Efficient Nanocatalyst of Fe₃O₄@SiO₂–APTES‐supported Trifluoroacetic Acid

Abstract

Fe3O4@SiO2–APTES‐supported trifluoroacetic acid nanocatalyst was used for the one‐pot synthesis of α‐aminonitriles via a three‐component reaction of aldehydes (or ketones), amines, and sodium cyanide. This method produced a high yield of 75–96% using only a small amount of the catalyst (0.05 g) in EtOH at room temperature. The catalyst was also employed for the synthesis of 5‐substituted 1H‐tetrazoles from nitriles and sodium azide in EtOH at 80°C. The tetrazoles were produced with good‐to‐excellent yields in a short reaction time of 4 h. Both synthetic methods were carried out in the absence of an organic volatile solvent. Because the supported trifluoroacetic acid generated a solid acid on the surface, thus the acid corrosiveness was not a serious challenge. This heterogeneous nanocatalyst was magnetically recovered and reused several times without significant loss of catalytic activity.

Zinc oxide nanoparticles coated with food colorant Brilliant black: Synthesis, characterization, and comparative DNA interaction and antibacterial activity studies

“…Afterward, the product was collected by centrifugation and washed thoroughly with ethanol. Finally, the collected product, ZnO@SiO 2 @APTES, was dried in an oven at 60°C for 8 hr (Fatahi et al., 2019).…”

Nanostructured silicate catalysts for environmentally benign Strecker-type reactions:status quoandquo vadis

“…Interestingly, Jafarzadeh et al 134 demonstrated that Fe 3 O 4 @SiO 2 @PrNH 2 -supported trifluoroacetic acid (CF 3 COOH, TFA), Fe 3 O 4 @SiO 2 @PrNH 2 . TFA works well as a nanocatalyst in the S-3-CR condensation of aldehydes (or ketones), amines, and sodium cyanide (but not TMSCN) in ethanol at room temperature to afford the respective tertiary or quaternary α-amino nitriles 27–28 (types I, III and IV).…”

“…Interestingly, Jafarzadeh et al 134 demonstrated that Fe 3 -O 4 @SiO 2 @PrNH 2 -supported triuoroacetic acid (CF 3 COOH, TFA), Fe 3 O 4 @SiO 2 @PrNH 2 .…”

Nanomaterial catalyzed green synthesis of tetrazoles and its derivatives: a review on recent advancements

“…The synthesized nano-catalyst produced target tetrazoles in excellent yields in short reaction time of 4 h. Along with this, nano catalyst was easily recovered from external magnet and reused several times without significant loss of catalytic activity. 48 Similarly, structurally diverse wide library of 5-substituted-1 H -tetrazoles drug-like molecules was synthesized by Ashraf et al by introducing new magnetic nano-catalyst Fe 3 O 4 @ l -lysine-Pd(0) catalyzed protocol ( Table 2 , entry 9). The Fe 3 O 4 @ l -lysine-Pd(0) catalyzed green sustainable protocol involved [3+2] cycloaddition reactions of various aryl nitriles (1.0 mmol) possessing either electron-withdrawing or electron-donating substituents with sodium azide (1.3 mmol) in water.…”