Synthesis of 1,4‐Dihydropyridines Bearing a Carbamate Moiety on the 4‐Position

Habibi, Davood; Safaee, Maliheh

doi:10.1155/2013/495982

Cited by 9 publications

(5 citation statements)

References 49 publications

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“…[19][20][21][22] Recently, organic compounds containing tetrazole moiety have attracted increasing attention due to their wide range of applications in various areas of science. [23,24] Especially in medicinal chemistry, [25] tetrazole rings have been utilized as bioisosteres for carboxyl groups owingto their similar properties. Therefore, the tetrazole moiety could be found in pharmaceutical materials, such as antihypertensive, antineoplastic, antibiotic, antiviral and antiallergic drugs.…”

Section: Introductionmentioning

confidence: 99%

Boehmite@SiO₂@ Tris (hydroxymethyl)aminomethane‐Cu(I): a novel, highly efficient and reusable nanocatalyst for the C‐C bond formation and the synthesis of 5‐substituted 1H‐tetrazoles in green media

Ghorbani‐Choghamarani

Aghavandi

Mohammadi

2020

Applied Organom Chemis

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In this work, a versatile protocol was introduced for the preparation of a new Cu(I) supported complex on Silica supported boehmite nanoparticles (Boehmite@SiO2@Tris‐Cu(I)). The structure of the catalyst was comprehensively characterized using Fourier transform infrared spectroscopy (FT‐IR), X‐Ray Diffractometer (XRD), energy‐dispersive X‐ray spectroscopy (EDS), inductively coupled plasma atomic emission spectroscopy (ICP), X‐ray mapping, thermogravimetric analysis (TGA) and scanning electron microscopy (SEM) techniques. The catalytic activity of this catalyst was studied in the Suzuki cross‐coupling reaction and synthesis of 5‐substituted 1H‐tetrazole derivatives in ethanol and PEG‐400 respectively as green solvents. In this sense, simple preparation of the catalyst from the commercially available materials, high catalytic activity, simple operation, short reaction times, high yields and use of green solvent are some advantages of this protocol. Finally, it is worth mentioning that this nanocatalyst was easily recovered, and reused for several times without significant loss of its catalytic efficiency. In addition, stability of the catalyst after recycling was confirmed by FT‐IR technique.

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Section: Introductionmentioning

confidence: 99%

Boehmite@SiO₂@ Tris (hydroxymethyl)aminomethane‐Cu(I): a novel, highly efficient and reusable nanocatalyst for the C‐C bond formation and the synthesis of 5‐substituted 1H‐tetrazoles in green media

Ghorbani‐Choghamarani

Aghavandi

Mohammadi

2020

Applied Organom Chemis

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“…This work presents the synthesis of a series of BRs carbamates analogs. Various hydroxysteroids (stigmasterol, β-sitosterol, diosgenin, and oxygenated derivatives) were condensed with phenyl isocyanate to afford the corresponding carbamates [ 31 ]. Post condensation reactions, i.e., epoxidation, carbonyl reduction, and oxime formation were used to introduce new diversification elements.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Steroidal Carbamates with Plant-Growth-Promoting Activity: Theoretical and Experimental Evidence

Pacheco

Ceballos

Castro

et al. 2021

IJMS

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A priority of modern agriculture is to use novel and environmentally friendly plant-growth promoter compounds to increase crop yields and avoid the indiscriminate use of synthetic fertilizers. Brassinosteroids are directly involved in the growth and development of plants and are considered attractive candidates to solve this problem. Obtaining these metabolites from their natural sources is expensive and cumbersome since they occur in extremely low concentrations in plants. For this reason, much effort has been dedicated in the last decades to synthesize brassinosteroids analogs. In this manuscript, we present the synthesis and characterization of seven steroidal carbamates starting from stigmasterol, β-sitosterol, diosgenin and several oxygenated derivatives of it. The synthesis route for functionalization of diosgenin included epoxidation and epoxy opening reactions, reduction of carbonyl groups, selective oxidation of hydroxyl groups, among others. All the obtained compounds were characterized by 1H and 13C NMR, HRMS, and their melting points are also reported. Rice lamina inclination test performed at different concentrations established that all reported steroidal carbamates show plant-growth-promoting activity. A molecular docking study evaluated the affinity of the synthesized compounds towards the BRI1-BAK1 receptor from Arabidopsis thaliana and three of the docked compounds displayed a binding energy lower than brassinolide.

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“…[26][27][28] In most of the cases, tetrazole heterocycles have been synthesized by [3 + 2] cycloaddition of aryl nitriles with sodium azide in the presence of homogeneous metal catalysts. [27,[29][30][31] But in the present work, we are concerned with the synthesis of 5-substituted 1H-tetrazole derivatives using L-lysine-Pd(0) catalytic complex functionalized magnetically separable nanocomposite as recyclable and reusable catalyst. The present work is probably the first report on the synthesis of 5-substituted 1H-tetrazole in the water as green solvent.…”

Section: Introductionmentioning

confidence: 99%

Fe₃O₄@L‐lysine‐Pd(0) organic–inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2 + 3] cycloaddition synthesis of 5‐substituted 1H‐tetrazoles

Ashraf

Liu

et al. 2020

Applied Organom Chemis

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An efficient and sustainable synthetic protocol has been presented to synthesis and 5-substituted 1H-tetrazole privileged heterocyclic substructures. The synthetic protocol involves two-component reaction between aryl nitriles and NaN 3 in water using complex of L-lysine-palladium nanoparticles (NPs) modified Fe 3 O 4 nanoparticles as magnetically separable, recyclable, and reusable heterogeneous catalyst. Magnetically retrievable L-lysine-Pd(0) modified Fe 3 O 4 nanoparticles were applied in [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles. The advantages of this strategy include easy recovery and efficient reusability of the expensive Pd NPs, obtaining high yields of [2 + 3] cycloaddition, short reaction times, and all of the reported synthetic strategies are being performed in water as green solvent for a wide range of substrates.

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Synthesis of 1,4‐Dihydropyridines Bearing a Carbamate Moiety on the 4‐Position

Cited by 9 publications

References 49 publications

Boehmite@SiO₂@ Tris (hydroxymethyl)aminomethane‐Cu(I): a novel, highly efficient and reusable nanocatalyst for the C‐C bond formation and the synthesis of 5‐substituted 1H‐tetrazoles in green media

Boehmite@SiO₂@ Tris (hydroxymethyl)aminomethane‐Cu(I): a novel, highly efficient and reusable nanocatalyst for the C‐C bond formation and the synthesis of 5‐substituted 1H‐tetrazoles in green media

Synthesis of New Steroidal Carbamates with Plant-Growth-Promoting Activity: Theoretical and Experimental Evidence

Fe₃O₄@L‐lysine‐Pd(0) organic–inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2 + 3] cycloaddition synthesis of 5‐substituted 1H‐tetrazoles

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Synthesis of 1,4‐Dihydropyridines Bearing a Carbamate Moiety on the 4‐Position

Cited by 9 publications

References 49 publications

Boehmite@SiO2@ Tris (hydroxymethyl)aminomethane‐Cu(I): a novel, highly efficient and reusable nanocatalyst for the C‐C bond formation and the synthesis of 5‐substituted 1H‐tetrazoles in green media

Boehmite@SiO2@ Tris (hydroxymethyl)aminomethane‐Cu(I): a novel, highly efficient and reusable nanocatalyst for the C‐C bond formation and the synthesis of 5‐substituted 1H‐tetrazoles in green media

Synthesis of New Steroidal Carbamates with Plant-Growth-Promoting Activity: Theoretical and Experimental Evidence

Fe3O4@L‐lysine‐Pd(0) organic–inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2 + 3] cycloaddition synthesis of 5‐substituted 1H‐tetrazoles

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Boehmite@SiO₂@ Tris (hydroxymethyl)aminomethane‐Cu(I): a novel, highly efficient and reusable nanocatalyst for the C‐C bond formation and the synthesis of 5‐substituted 1H‐tetrazoles in green media

Boehmite@SiO₂@ Tris (hydroxymethyl)aminomethane‐Cu(I): a novel, highly efficient and reusable nanocatalyst for the C‐C bond formation and the synthesis of 5‐substituted 1H‐tetrazoles in green media

Fe₃O₄@L‐lysine‐Pd(0) organic–inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2 + 3] cycloaddition synthesis of 5‐substituted 1H‐tetrazoles