scholarly journals Full N,N-Methylation of 4,4′-Methylenedianiline with Dimethyl Carbonate: A Feasible Access to 4,4′-Methylene bis(N,N-Dimethylaniline)

2018 ◽  
Vol 2018 ◽  
pp. 1-10
Author(s):  
Zegang Qiu ◽  
Kunjie Wang ◽  
Zhiqin Li ◽  
Tao Li ◽  
Jinhao Bai ◽  
...  
Keyword(s):  
Zinc Acetate ◽  
Dimethyl Carbonate ◽  
Reaction Pathway ◽  
Major Product ◽  
High Yield ◽  
Synthetic Route ◽  
Reaction Conditions ◽  
High Yields ◽  
By Products

The full N,N-methylation of 4,4′-methylenedianiline (MDA) with dimethyl carbonate (DMC) was investigated. The yield of the major product 4,4′-methylene bis(N,N-dimethylaniline) (MBDMA) reached as high as 97% over NaY catalyst at 190°C for 6 h. The catalyst could be used for two more times with acceptable MBDMA yields higher than 90%. The main by-products were identified as three N-methylated derivatives. Surprisingly, the formation of the N-methoxycarbonylation product was extremely restrained, which could be produced in high yields of 98% on zinc acetate catalyst. Furthermore, the reaction pathway to the major product MBDMA was proposed. Finally, a feasible synthetic route of 4,4′-methylene bis(N,N-dimethylaniline) (MBDMA) was established, featuring a high yield, mild reaction conditions, and simple operations.

scholarly journals A two step synthesis of a key unit B precursor of cryptophycins by asymmetric hydrogenation

2011 ◽  
Vol 7 ◽  
pp. 243-245 ◽  
Author(s):  
Benedikt Sammet ◽  
Mathilde Brax ◽  
Norbert Sewald
Keyword(s):  
Asymmetric Hydrogenation ◽  
Synthetic Route ◽  
Reaction Conditions ◽  
High Yields

A novel highly enantioselective two step access to a unit B precursor of cryptophycins in good yields from commercially available starting materials has been developed. The key step is an asymmetric hydrogenation using the commercially available [(COD)Rh-(R,R)-Et-DuPhos]BF4 catalyst. The synthetic route provides the advantage of less synthetic steps, proceeds with high yields and enantioselectivity, and avoids hazardous reaction conditions.

A facile synthetic route for antineoplastic drug GDC-0449

2014 ◽  
Vol 68 (10) ◽  
Author(s):  
Meng Cao ◽  
Hua-You Hu ◽  
Hu-Cheng Zhao ◽  
Xi-Quan Zhang ◽  
Hong-Mei Gu ◽  
...  
Keyword(s):  
Nitro Group ◽  
Intermediate Product ◽  
Cross Coupling ◽  
Antineoplastic Drug ◽  
High Yield ◽  
Synthetic Route ◽  
Reaction Conditions ◽  
Final Compound

AbstractIn the current study a facile synthetic route for preparing antineoplastic drug GDC-0449 is investigated. Starting with pyridine-1-oxide and 1-iodo-3-nitrobenzene, the intermediate product 2-(2-chloro-5-nitrophenyl) pyridine was prepared by cross-coupling, deoxidation and halogenation. The final compound was then synthesised by reduction of the nitro group followed by amidation. This synthetic route avoids the use of unstable organometallic or organic boride compounds; it employs relatively inexpensive and bench-stable reagents, involves readily controllable reaction conditions, and achieves a relatively high yield.

Highly Efficient and Reusable Pd/AlO(OH) Catalyzed Synthesis of Acridinedione Derivatives

2019 ◽  
Vol 6 (3) ◽  
pp. 257-265
Author(s):  
Benan Kilbas ◽  
Sinem Ergen ◽  
Davut Cakici
Keyword(s):  
Biological Activities ◽  
Reaction Medium ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Highly Active ◽  
Heterogenous Catalyst ◽  
Ultrasound System ◽  
High Yields ◽  
Temperature Time

Background: Synthesis of acridinedione derivatives via one-pot multi-component approaches using highly active and reusable Pd/AlO(OH) heterogenous catalyst was studied. This process provided a convenient method to obtain various acridinediones with potential biological activities. The reactions were performed in mild conditions such as low temperature and short reaction time with desirable yields. Methods: Commercially available Pd/AlO(OH) nanoparticles characterized by XRD and SEM methods were afforded for the synthesis of acridinedione derivatives with high yields. Crude products were analyzed by GC and 1H NMR. The reactions were completed within 1h at 40°C by the assistance of ultrasound system. Results: Optimization of reaction conditions is of critical case for successful synthesis. Solvent, temperature, time and amount of catalyst were studied. At the end of the experiments, the synthesis of 1 mmol of acridinedione was optimized by using 25 mg of Pd/AlO(OH) NPs, 3 ml of DMF for 60 min at 40°C in the ultrasound system. An experimental work to check the reusability of the catalyst was also studied. Pd/Al(O)OH catalyst in the first run was higher than that of the reused catalyst in the fifth run. ICP-OES analyses showed palladium leaching into the reaction medium was only 1.1% which is negligible. Nanocatalyst employed a high activity and good reusability. Conclusion: A convenient and versatile method was developed for the synthesis of acridinediones in a mild condition with absolute conversion and high yield using ultrasound system in the presence of nanocatalyst.

A highly efficient CuI nanoparticles-catalyzed synthesis of tetrahydrochromenediones and dihydropyrano[c]chromenediones under grinding

2016 ◽  
Vol 71 (7) ◽  
pp. 777-782 ◽  
Author(s):  
Shahrzad Abdolmohammadi ◽  
Reza Ghiasi ◽  
Sam Ahmadzadeh-Vatani
Keyword(s):  
Aromatic Aldehyde ◽  
Condensation Reaction ◽  
Solvent Free ◽  
New Method ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Grinding Conditions ◽  
High Yields ◽  
Active Methylene ◽  
By Products

AbstractA concise and CuI nanoparticle-catalyzed synthesis of tetrahydrochromenediones and dihydropyrano[c]chromenediones under solvent-free grinding conditions via the three-component condensation reaction of Meldrum’s acid, an aromatic aldehyde, and an active methylene compound, including dimedone or 4-hydroxycoumarin, was developed. This new method gives desirable advantages such as simple reaction setup, very mild reaction conditions, production of the desired products in high yields without by-products, recyclability of the catalyst, and environmentally benign procedure.

scholarly journals An Efficient Synthesis of Milnacipran Hydrochloride via Reductive Amination of Aldehyde

2017 ◽  
Vol 2017 ◽  
pp. 1-6
Author(s):  
Neha Reddy Desireddy ◽  
Arava Glory ◽  
Krishna Reddy Bhimireddy ◽  
Yadagiri Kurra ◽  
Ram Reddy
Keyword(s):  
Primary Amine ◽  
Reductive Amination ◽  
Major Product ◽  
Important Application ◽  
Water Soluble ◽  
High Yield ◽  
Efficient Synthesis ◽  
By Products

An efficient synthesis of milnacipran hydrochloride has been accomplished. The important application of this paper is the reductive amination of aldehyde to primary amine with water soluble reagents. This method provides a high yield of primary amine as the major product, reduces the number of steps, and discourages by-products.

scholarly journals Dialkyl Succinates and Adipates as Alternative Plasticizers—Even More Efficient Synthesis

Materials ◽  
2021 ◽  
Vol 14 (20) ◽  
pp. 6219
Author(s):  
Natalia Barteczko ◽  
Justyna Więcławik ◽  
Anna Tracz ◽  
Ewa Pankalla ◽  
Karol Erfurt ◽  
...  
Keyword(s):  
Simple Procedure ◽  
Product Formation ◽  
Liquid System ◽  
Industrial Applications ◽  
Molar Ratio ◽  
High Yield ◽  
Reaction Conditions ◽  
Two Phase ◽  
Phase Liquid ◽  
High Yields

As a result of strict regulations of phthalate plasticizers, alternative non-phthalate forms are desired and increasingly used. This work presents a synthetic method for alternative plasticizers (dialkyl succinates and adipates) via esterification of succinic and adipic acid with alcohols: butan-1-ol and 2-ethylhexan-1-ol. Ionic liquids were synthesized by the reaction of triethylamine with over-equimolar (1:2.7) amounts of sulfuric(VI) acid, which were used as an acidic catalyst and solvent. The two-phase liquid–liquid system was formed during the reaction due to immiscibility of the esters with the ionic liquid. This phenomenon is a driving force of this process, shifting the equilibrium toward the product formation. As a result, dialkyl succinates and adipates were obtained in high yields (99%) and selectivities (>99%), under mild reaction conditions at 70–80 °C and using a 4:1 molar ratio of alcohol to acid and 15 mol% of catalyst. The catalyst was recycled 10 times without any loss of activity. This alternative method is highly competitive: it involves a simple procedure for product isolation as well as a high yield and purity of the resulting esters. These advantages make this method sustainable and promising for industrial applications.

Comparison Of Reaction Pathway And Product Analysis For Hydroxyalkylation Of Parabanic Acid With Oxiranes And Alkylene Carbonates

e-Polymers ◽  
2007 ◽  
Vol 7 (1) ◽  
Author(s):  
Iwona Zarzyka-Niemiec
Keyword(s):  
Reaction Pathway ◽  
Product Analysis ◽  
Reaction Conditions ◽  
Maldi Tof ◽  
By Products

AbstractReactions of parabanic acid (PA) with ethylene and propylene oxides and carbonates lead to oligomeric products with hydroxyalkyl groups in both cases. The parabanic acid ring undergoes scissions during reactions depending on kind of reagent and reaction conditions. In some cases the trioxoimidazolidine ring remains untouched. Using the MALDI ToF technique the product analysis was performed. The by-products were determined quantitatively by GC. The thermostability of oligomeric products was also determined.

Synthesis and Properties of 5-Hydroxymethyl-2′-deoxyuridine and its α-Anomer

1971 ◽  
Vol 49 (5) ◽  
pp. 719-724 ◽  
Author(s):  
V. S. Gupta ◽  
G. L. Bubbar
Keyword(s):  
Absorption Spectra ◽  
Elemental Analysis ◽  
Mercuric Chloride ◽  
Room Temperature ◽  
Major Product ◽  
High Yield ◽  
Crystalline Solid ◽  
Fusion Method ◽  
Excellent Yield ◽  
High Yields

The synthesis and properties of 5-hydroxymethyldeoxyuridine (6) and its α-anomer 7 are described. Treatment of 5-hydroxymethyluracil (2) with trimethylchlorosilane in the presence of triethylamine gave 2,4,5-tris(trimethylsilyl)-5-oxymethyluracil (3) in excellent yield (92%) which, upon condensation with 3,5-di-(O-p-toluoyl)-2-deoxy-D-ribofuranosyl chloride in acetonitrile at room temperature, furnished an anomeric mixture of substituted nucleosides β-anomer (4) and α-anomer (5) in high yield 90% (by a fusion method (12) yield of blocked nucleosides was 70%). Compound 4 was the major product formed by both methods and was recovered as a crystalline solid in high yield. However, condensation of 3 with chlorosugar in benezene with mercuric chloride as a catalyst at room temperature gave a mixture of protected nucleosides; the amount of 5 formed was appreciably higher (34%) and was isolated as a microcrystalline solid from mother liquors in low yield (without the catalyst nucleosides were formed in low yield 30%). Removal of the blocking groups by alcoholysis gave 6 and 7 in high yields. The structure was confirmed by n.m.r. studies, u.v. and i.r. absorption spectra, elemental analysis, and by conversion of 4 to β-thymidine (8).

Evaluation of germ plasm for resistant to Soybean mosaic virus (SMV)

2020 ◽  
Vol 21 (1) ◽  
pp. 6-9
Author(s):  
Wuye Ria Andayanie
Keyword(s):  
Abiotic Stress ◽  
Environmental Factors ◽  
Mosaic Virus ◽  
Polyclonal Antibody ◽  
Symptom Severity ◽  
Germ Plasm ◽  
Polyclonal Antibodies ◽  
Soybean Mosaic Virus ◽  
High Yield ◽  
High Yields

Soybean superior varieties with high yields and are resistant to abiotic stress have been largely released, although some varieties grown in the field are not resistant to SMV. In addition, the opportunity to obtain lines of hope as prospective varieties with high yield and resistance to SMV is very small. The method for evaluating soybean germplasm is based on serological observations of 98 accessions of leaf samples from SMV inoculation with T isolate. The evaluation results of 98 accessions based on visual observations showed 31 genotypes reacting very resistant or healthy to mild resistant category to SMV T isolate  with a percentage of symptom severity of 0 −30 %. Among 31 genotypes there are 2 genotypes (PI 200485; M8Grb 44; Mlg 3288) with the category of visually very resistant and resistant, respectively and  Mlg 3288  with the category of mild resistant.  They have a good agronomic appearance with a weight of 100 seeds (˃10 g) and react negatively with polyclonal antibodies to SMV, except Mlg 3288 reaction is not consistent, despite the weight of 100 seeds (˃ 10 g). Leaf samples from 98 accessions revealed various symptoms of SMV infection in the field. This diversity of symptoms is caused by susceptibility to accession, when infection occurs, and environmental factors. Keywords—: soybean; genotipe; Soybean mosaic virus (SMV); disease severity; polyclonal  antibody

Gold Catalyzed Hydroamination of Propargylic Alcohols: Controlling Divergent Reaction Pathways to Access 1,3-Aminoalcohols, 3-Hydroxyketones or 3-Aminoketones

2018 ◽  
Author(s):  
Victor Laserna ◽  
Tom Sheppard
Keyword(s):  
Gold Catalysis ◽  
Reaction Pathways ◽  
High Yield ◽  
Reaction Conditions ◽  
Propargylic Alcohols ◽  
Catalytic Quantity ◽  
Selective Formation ◽  
General Method

A versatile approach to the valorization of propargylic alcohols is reported, enabling controlled access to three different products from the same starting materials. Firstly, a general method for the hydroamination of propargylic alcohols with anilines is described using gold catalysis to give 3-hydroxy imines with complete regioselectivity. These 3-hydroxyimines can be reduced to give 1,3-aminoalcohols with high syn seletivity. Alternatively, by using a catalytic quantity of aniline, 3-hydroxyketones can be obtained in high yield directly from propargylic alcohols. Further manipulation of the reaction conditions enables the selective formation of 3-aminoketones via a rearrangement/hydroamination pathway.<br>

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