scholarly journals A Study on N-Substituted Nortropinone Synthesis using Acetone Equivalents

2020 ◽  
Vol 32 (5) ◽  
pp. 1145-1150
Author(s):  
J.H. Song ◽  
S.M. Bae ◽  
S.K. Cho ◽  
J.H. Cho ◽  
D.I. Jung

Robinson′s synthesis has long been a classic in organic chemistry due to its simplicity and impact in the industry. Various modifications have been made to improve the system. Among them, replacing acetone with more acidic chemical equivalents such as calcium dicarboxylic acid or ethyl dicarboxylic acetone improved the yield. In line with this trend, our group previously reported the synthesis of mono- and di-N-substituted tropinone derivatives from the one-pot reaction of 2,5-dimethoxy tetrahydrofuran and various amines with acetonedicarboxylic acid in the presence of HCl and water at room temperature. In this study, the synthesis with acetone instead of acetone-dicarboxylic acid was examined. Mono- and di-N-substituted nortropinones were prepared in higher yields in all cases although there were extent to which yields increased depending on the nature of substituents

2018 ◽  
Author(s):  
Huong T. D. Nguyen ◽  
Y B. N. Tran ◽  
Hung N. Nguyen ◽  
Tranh C. Nguyen ◽  
Felipe Gándara ◽  
...  

<p>Three novel lanthanide metal˗organic frameworks (Ln-MOFs), namely MOF-590, -591, and -592 were constructed from a naphthalene diimide tetracarboxylic acid. Gas adsorption measurements of MOF-591 and -592 revealed good adsorption of CO<sub>2</sub> (low pressure, at room temperature) and moderate CO<sub>2</sub> selectivity over N<sub>2</sub> and CH<sub>4</sub>. Accordingly, breakthrough measurements were performed on a representative MOF-592, in which the separation of CO<sub>2</sub> from binary mixture containing N<sub>2</sub> and CO<sub>2</sub> was demonstrated without any loss in performance over three consecutive cycles. Moreover, MOF-590, MOF-591, and MOF-592 exhibited catalytic activity in the one-pot synthesis of styrene carbonate from styrene and CO<sub>2</sub> under mild conditions (1 atm CO<sub>2</sub>, 80 °C, and solvent-free). Among the new materials, MOF-590 revealed a remarkable efficiency with exceptional conversion (96%), selectivity (95%), and yield (91%). </p><br>


2020 ◽  
Vol 24 (4) ◽  
pp. 465-471 ◽  
Author(s):  
Zita Rádai ◽  
Réka Szabó ◽  
Áron Szigetvári ◽  
Nóra Zsuzsa Kiss ◽  
Zoltán Mucsi ◽  
...  

The phospha-Brook rearrangement of dialkyl 1-aryl-1-hydroxymethylphosphonates (HPs) to the corresponding benzyl phosphates (BPs) has been elaborated under solid-liquid phase transfer catalytic conditions. The best procedure involved the use of triethylbenzylammonium chloride as the catalyst and Cs2CO3 as the base in acetonitrile as the solvent at room temperature. The substrate dependence of the rearrangement has been studied, and the mechanism of the transformation under discussion was explored by quantum chemical calculations. The key intermediate is an oxaphosphirane. The one-pot version starting with the Pudovik reaction has also been developed. The conditions of this tandem transformation were the same, as those for the one-step HP→BP conversion.


SynOpen ◽  
2021 ◽  
Author(s):  
Mina Ghassemi ◽  
Ali Maleki

Copper ferrite (CuFe2O4) magnetic nanoparticles (MNPs) were synthesized via thermal decomposition method and applied as a reusable and green catalyst in the synthesis of functionalized 4H-pyran derivatives using malononitrile, an aromatic aldehyde and a β-ketoester in ethanol at room temperature. Then it was characterized by Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX) analysis, scanning electron microscopy (SEM) images, thermo gravimetric and differential thermo gravimetric (TGA/DTG) analysis. The catalyst was recovered from the reaction mixture by applying an external magnet and decanting the mixture. Recycled catalyst was reused for several times without significant loss in its activity. Running the one-pot three-component reaction at room temperature, no use of eternal energy source and using a green solvent provide benign, mild, and environmentally friendly reaction conditions; as well, ease of catalyst recovering, catalyst recyclability, no use of column chromatography and good to excellent yields are extra advantages of this work.


2010 ◽  
Vol 8 (2) ◽  
pp. 320-325 ◽  
Author(s):  
Santosh Katkar ◽  
Pravinkumar Mohite ◽  
Lakshman Gadekar ◽  
Balasaheb Arbad ◽  
Machhindra Lande

AbstractA rapid and an efficient one-pot method for the synthesis of quinoxalines catalysed by ZnO-beta zeolite at room temperature is described. This environmentally benign method provides several advantages over methods that are currently employed such as a simple work-up, mild reaction conditions, good to excellent yields, and a process to recover and reuse the catalyst for several cycles with consistent activity.


RSC Advances ◽  
2015 ◽  
Vol 5 (49) ◽  
pp. 39263-39269 ◽  
Author(s):  
Goutam Brahmachari ◽  
Bubun Banerjee

Ceric ammonium nitrate (CAN)-catalyzed one-pot synthesis of alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl)methane scaffolds (3a–3u) has been developed via a pseudo three-component reaction in aqueous ethanol at room temperature.


2018 ◽  
Author(s):  
Huong T. D. Nguyen ◽  
Y B. N. Tran ◽  
Hung N. Nguyen ◽  
Tranh C. Nguyen ◽  
Felipe Gándara ◽  
...  

<p>Three novel lanthanide metal˗organic frameworks (Ln-MOFs), namely MOF-590, -591, and -592 were constructed from a naphthalene diimide tetracarboxylic acid. Gas adsorption measurements of MOF-591 and -592 revealed good adsorption of CO<sub>2</sub> (low pressure, at room temperature) and moderate CO<sub>2</sub> selectivity over N<sub>2</sub> and CH<sub>4</sub>. Accordingly, breakthrough measurements were performed on a representative MOF-592, in which the separation of CO<sub>2</sub> from binary mixture containing N<sub>2</sub> and CO<sub>2</sub> was demonstrated without any loss in performance over three consecutive cycles. Moreover, MOF-590, MOF-591, and MOF-592 exhibited catalytic activity in the one-pot synthesis of styrene carbonate from styrene and CO<sub>2</sub> under mild conditions (1 atm CO<sub>2</sub>, 80 °C, and solvent-free). Among the new materials, MOF-590 revealed a remarkable efficiency with exceptional conversion (96%), selectivity (95%), and yield (91%). </p><br>


2021 ◽  
pp. 221-234
Author(s):  
Marwa M. Abdeen ◽  
Mohamed A. Hamed ◽  
Abdel Aleem Hassan Abdel Aleem ◽  
Ibrahim F. Nassar ◽  
Ibrahim E.T. El-Sayed

Different metal catalysts have been tested for the one-pot transformation of carbonyl compounds, amines and phosphites to α-aminophosphonates. The influence of catalyst type, amount, solvent and the substrate electronic factor have been investigated. The results revealed that the carbonyl compounds could be smoothly converted into α-aminophosphonates at room temperature in good to excellent yields, with or without solvent in a reasonable reaction time. These results suggested that among others, lithium perchlorate and metal triflates were proven to be effective catalysts in 10 moles % catalysts. Polar aprotic solvents proved to be the best for the synthesis of α-aminophosphonates. The synthesized compounds' structure characterizations were elucidated by different spectroscopic tools and showed results consistent with the expected structures.


2016 ◽  
Vol 71 (1) ◽  
pp. 31-36 ◽  
Author(s):  
Kobra Nikoofar ◽  
Zahra Khalili

AbstractSymmetrical and unsymmetrical 3,3-di(aryl)indolin-2-ones have been synthesized by nano-SiO2 as green, heterogeneous, and reusable catalyst under solvent-free conditions at room temperature via magnetic stirring and grinding methods. A plausible mechanism of condensation has also been presented.


1991 ◽  
Vol 46 (8) ◽  
pp. 978-984 ◽  
Author(s):  
Joseph Grobe ◽  
Duc Le Van ◽  
Thomas Großpietsch

The reaction of perfluoro-2-phosphapropene F3CP=CF2 (1) with tert-butylamine or isopropylamine in a 1:3 molar ratio leads to the novel iminomethylene phosphanes F3CP=C=N(tBu) [(2), 30% yield] and F3CP=C=N(iPr) [(3), 5%], respectively. 2 slowly decomposes at room temperature giving tert-butylisonitrile and the cyclophosphanes (F3CP)n (n = 3, 4, 5). 3 is found to be less stable than 2 and for example is attacked by primary amines. The reaction of 2 with 2,3-dimethyl-1,3-butadiene or trimethylphosphane yields, on the one hand, the cycloaddition product of bis(trifluormethyl)diphosphene (4), and on the other hand, the phosphorus ylid Me3P=PCF3 (5) together with (tBu)NC.2 and 3, respectively, are not obtained from (F3C)2PH and the corresponding primary amines in a series of HF elimination and H2NR addition reactions. The main products formed from a 1:4 molar mixture of (F3C)2PH and H2N(iPr) in a one-pot procedure were shown to be the chiral phosphanes F3CP[NH(iPr)]C[=N(iPr)]H (6), F3CP[NH(iPr)]CHF2 (7) and F3CP[NH(iPr)]CH2F (8) (60:35:5). The corresponding reaction of (F3C)2PH with H2N(tBu) mainly yields the compound F3CP[NH(tBu)]CH2F (10).


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