Biomimetic approach for the synthesis of N,N′-diarylsubstituted formamidines catalyzed by β-cyclodextrin in water

Patil, Dipak R.; Dalal, Dipak S.

doi:10.1016/j.cclet.2012.08.003

Cited by 26 publications

(8 citation statements)

References 25 publications

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“…synthesized formamidine complex in reflux conditions and low yield of product with acetic acid as a liquid acid catalyst ( Table 2 , entry 6) [ 85 ]. The reaction with cyclodextrin (CD) as a catalyst ( Table 2 , entry 7) [ 86 ] was done at more time (14 h). It was revealed that Fe 2 O 3 @SiO 2 –SO 3 H nanofibers as a novel magnetic catalyst performed this reaction in a shorter time and with higher efficiency.…”

Section: Resultsmentioning

confidence: 99%

“… Temp. (°C) Time Yield 1 Fe 2 O 3 @SiO 2 –SO 3 H nanofibers (3 mol%) 70 1 h 96 2 Fe 2 O 3 @SiO 2 –SO 3 H nanofibers (1 mol%) r.t. 3 h 86 3 Fe 2 O 3 @SiO 2 -HCLO 4 nanoparticles (2.5 mol%) [ 15 ] r.t. 4 h 51 4 Fe 2 O 3 @SiO 2 –HBF 4 nanoparticles (2.5 mol%) [ 15 ] r.t. 4 h 95 5 RH- SO 3 H (50 mg) [ 84 ] 60 1 min 93 6 Acetic acid [ 85 ] 140–160 3–4 h 50–80 7 b-CD (2 mmol) [ 86 ] r.t. 14 h 92 …”

Section: Resultsmentioning

confidence: 99%

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The synthesis and characterization of Fe2O3@SiO2–SO3H nanofibers as a novel magnetic core-shell catalyst for formamidine and formamide synthesis

Ziyadi

Baghali²,

Heydari

2021

Heliyon

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Over the past several decades, the fabrication of novel ceramic nanofibers applicable in different areas has been a frequent focus of scientists around the world. Aiming to introduce novel ceramic core-shell nanofibers as a magnetic solid acid catalyst, Fe 2 O 3 @SiO 2 –SO 3 H magnetic nanofibers were prepared in this study using a modification of Fe 2 O 3 @SiO 2 core-shell nanofibers with chlorosulfonic acid to increase the acidic properties of these ceramic nanofibers. The products were characterized by scanning electron microscope (SEM), transmission electron microscope (TEM), energy dispersive X-ray spectroscope (EDS), vibrating sample magnetometer (VSM), X-ray diffraction (XRD) and Fourier transform infrared spectroscopy (FT-IR). The prepared nanofibers were used as catalysts in formamide and formamidine synthesis. The treatment of aqueous formic acid using diverse amines with a catalytic amount of Fe 2 O 3 @SiO 2 –SO 3 H nanofibers as a reusable, magnetic and heterogeneous catalyst produced high yields of corresponding formamides at room temperature. Likewise, the reaction of diverse amines with triethyl orthoformate led to the synthesis of formamidine derivatives in excellent yields using this novel catalyst. The catalytic system was able to be recovered and reused at least five times without any catalytic activity loss. Thus, novel core-shell nanofibers can act as efficient solid acid catalysts in different organic reactions capable of being reused several times due to their easy separation by applying magnet.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

The synthesis and characterization of Fe2O3@SiO2–SO3H nanofibers as a novel magnetic core-shell catalyst for formamidine and formamide synthesis

Ziyadi

Baghali²,

Heydari

2021

Heliyon

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“…102 [48] C 102 [19] ( reaction was completed, water was added to the reaction mixture in order to dissolve the catalyst. Then the reaction mixture was filtered off and the filtrate was evaporated under vacuum up to 70°C to the white solid residue achieved.…”

Section: Entrymentioning

confidence: 99%

“…In recent decades, N, N'-diaryl formamidines and their anions have been widely used in various fields of organic and medicinal chemistry. [18][19][20][21] These types of compounds have many biological and pharmaceutical properties, including antimalarial, [22] anesthetic, [23] ultraviolet light absorbent, [24] antihypertensive, [25] and renal dipeptidase inhibitory [26] activities.…”

Section: Introductionmentioning

confidence: 99%

Introduction of Two New Brønsted Acidic Ionic Liquids for the Formamide and Formamidine Derivatization of Amines

et al. 2020

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In this study, two recently reported 1,4-diazabicyclo[2.2.2] octane (DABCO)-based ionic liquids were used for the acceleration of the N-formylation of primary and secondary amines with formic acid under solvent-free conditions. These reagents have also been used for the efficient synthesis of N, N'-diaryl formamidines through reaction of triethyl orthoformate with primary aryl amines. These methods offer several advantages such as excellent yields, short reaction times and simple workup with the environmentally friendly procedure.

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“…13 Herein, we report a new, selective, one-pot, multicomponent synthesis of bioactive formamidines constructed on the 5-amino-3-anilinopyrazole-4-carbonitrile scaffold. The synthesis of simple symmetric formamidines by using a multicomponent reaction of anilines and triethyl orthoformate has been well documented in the literature since the report of a general methodology by Taylor et al 14 This reaction has been well explored and was found to proceed effectively under catalysis by cerium(IV) ammonium nitrate, 15 βcyclodextrin, 16 sulphated zirconia, 17 and γ-Fe 2 O 3 @SiO 2 -HA. 18 Good results were also obtained when hexafluoroisopropanol 19 or deep eutectic mixtures [tin(II) chloride-choline chloride] 20 were used as solvents.…”

mentioning

confidence: 99%

A New, One-Pot, Multicomponent Synthesis of Bioactive N-Pyrazolylformamidines under Microwave Irradiation

2016

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A one-pot, three-component, microwave-assisted reaction of polysubstituted 5-aminopyrazoles, triethyl orthoformate, and a series of cyclic secondary amines was developed and successfully employed for the synthesis of novel N-pyrazolylformamidines. Under catalyst-free conditions, the reaction proceeded in a chemo-and regioselective manner, resulting in the formation of unsymmetric formamidines, which were isolated in high yields and purity. Some of the prepared compounds were found to inhibit interleukin-17 secretion in phenotypic in vitro assays.

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Biomimetic approach for the synthesis of N,N′-diarylsubstituted formamidines catalyzed by β-cyclodextrin in water

Cited by 26 publications

References 25 publications

The synthesis and characterization of Fe2O3@SiO2–SO3H nanofibers as a novel magnetic core-shell catalyst for formamidine and formamide synthesis

The synthesis and characterization of Fe2O3@SiO2–SO3H nanofibers as a novel magnetic core-shell catalyst for formamidine and formamide synthesis

Introduction of Two New Brønsted Acidic Ionic Liquids for the Formamide and Formamidine Derivatization of Amines

A New, One-Pot, Multicomponent Synthesis of Bioactive N-Pyrazolylformamidines under Microwave Irradiation

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