scholarly journals Silver(I) as a widely applicable, homogeneous catalyst for aerobic oxidation of aldehydes toward carboxylic acids in water—“silver mirror”: From stoichiometric to catalytic

2015 ◽  
Vol 1 (2) ◽  
pp. e1500020 ◽  
Author(s):  
Mingxin Liu ◽  
Haining Wang ◽  
Huiying Zeng ◽  
Chao-Jun Li
Keyword(s):  
Natural Products ◽  
Carboxylic Acids ◽  
Atmospheric Oxygen ◽  
Aerobic Oxidation ◽  
Aromatic Aldehydes ◽  
Catalyst Loading ◽  
Homogeneous Catalyst ◽  
Reaction Conditions ◽  
Silver Mirror ◽  
High Yields

The first example of a homogeneous silver(I)-catalyzed aerobic oxidation of aldehydes in water is reported. More than 50 examples of different aliphatic and aromatic aldehydes, including natural products, were tested, and all of them successfully underwent aerobic oxidation to give the corresponding carboxylic acids in extremely high yields. The reaction conditions are very mild and greener, requiring only a very low silver(I) catalyst loading, using atmospheric oxygen as the oxidant and water as the solvent, and allowing gram-scale oxidation with only 2 mg of our catalyst. Chromatography is completely unnecessary for purification in most cases.

Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde

2018 ◽  
Vol 21 (4) ◽  
pp. 298-301 ◽  
Author(s):  
Ghasem Marandi
Keyword(s):  
Biological Sciences ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
High Performance ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
New Materials ◽  
One Pot ◽  
High Yields ◽  
Benzaldehyde Derivatives

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

Three-Component Synthesis of 4-Arylidene-3-alkylisoxazol-5(4H)-ones in the presence of potassium 2,5-dioxoimidazolidin-1-ide

2021 ◽  
Vol 25 ◽  
Author(s):  
Neda Reihani ◽  
Hamzeh Kiyani
Keyword(s):  
Ethylene Glycol ◽  
Ethyl Acetoacetate ◽  
Reaction Medium ◽  
Hydroxylamine Hydrochloride ◽  
Aromatic Aldehydes ◽  
Catalyst Loading ◽  
Efficient Synthesis ◽  
Current Process ◽  
High Yields ◽  
Low Catalyst Loading

: An efficient synthesis of 4-arylidene-3-alkylisoxazole-5(4H)-ones has been implemented via the three-component cyclocondensation of aryl(heteroaryl)aldehydes with hydroxylamine hydrochloride and β-ketoesters. The potassium 2,5-dioxoimidazolidin-1-ide has been introduced as the new organocatalyst to facilitate of this heterocyclization. In the current process, three starting materials, including substituted benzaldehydes/heterocyclic aromatic aldehydes, hydroxylamine hydrochloride, and ethyl acetoacetate/propyl acetoacetate/butyryl acetoacetate have been successfully used for the synthesize of the number of substituted isoxazole-5(4H)-ones in good to high yields in ethylene glycol as a green reaction medium at 80 ºC. The low catalyst loading is also a main advantage over the some reported catalysts.

scholarly journals A Solvent-Free Protocol for the Green Synthesis of 5-Arylidene-2,4-thiazolidinediones Using Ethylenediamine Diacetate as Catalyst

2012 ◽  
Vol 2012 ◽  
pp. 1-5 ◽  
Author(s):  
Yuliang Zhang ◽  
Zhongqiang Zhou
Keyword(s):  
Knoevenagel Condensation ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Reusable Catalyst ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Solvent Free Conditions ◽  
High Yields ◽  
Work Up ◽  
Solvent Free Reaction

A simple and efficient synthesis of 5-arylidene-2,4-thiazolidinediones by the Knoevenagel condensation of aromatic aldehydes with 2,4-thiazolidinedione catalyzed by ethylenediamine diacetate under solvent-free conditions is described. The major advantages of this method are simple experimental and work-up procedures, solvent-free reaction conditions, small amount of catalyst, short reaction time, high yields, and utilization of an inexpensive and reusable catalyst.

One Pot Three Component Synthesis of 9-arylpolyhydroacridine Derivatives in an Ionic Liquid Medium

2005 ◽  
Vol 2005 (9) ◽  
pp. 600-602 ◽  
Author(s):  
Yu-Ling Li ◽  
Mei-Mei Zhang ◽  
Xiang-Shan Wang ◽  
Da-Qing Shi ◽  
Shu-Jiang Tu ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Ammonium Acetate ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
High Yields ◽  
Work Up ◽  
Ionic Liquid Medium

In this paper the preparation of 3,3,6,6-tetramethyl-9-aryl-1,2,3,4,5,6,7,8,9,10- decahydroacridin-1,8-dione derivatives from aromatic aldehydes, 5,5-dimethyl-1,3- cyclohexanedione and ammonium acetate in ionic liquids [bmim+][BF4-] is described. This new method has the advantages of easier work-up, milder reaction conditions, high yields and an environmentally benign procedure compared with other methods.

scholarly journals Synthesis of biscoumarin derivatives by the reaction of aldehydes and 4-hydroxycoumarin using ruthenium (III) chloride hydrate as a versatile homogeneous catalyst

2012 ◽  
Vol 77 (4) ◽  
pp. 407-413 ◽  
Author(s):  
Khalil Tabatabaeian ◽  
Hannaneh Heidari ◽  
Alireza Khorshidi ◽  
Manouchehr Mamaghani ◽  
Nosrat Mahmoodi
Keyword(s):  
Michael Reaction ◽  
Aqueous Media ◽  
Environmentally Benign ◽  
Homogeneous Catalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
The One ◽  
High Yields ◽  
Chloride Hydrate ◽  
Short Times

The one-pot domino Knoevenagel-type condensation/Michael reaction of aromatic, heteroaromatic and aliphatic aldehydes with 4-hydroxycoumarin in aqueous media in the presence of ruthenium salt as homogeneous catalyst was investigated. It was found that 5 mol% of RuCl3.nH2O catalyzes biscoumarin synthesis in high yields (70-95%) under optimised, mild, green and environmentally benign reaction conditions in short times (25-35min).

scholarly journals Tyrosine and Drug-like Late-stage Benzylic Functionalization via Photoredox Catalysis

2020 ◽  
Author(s):  
Tobias Brandhofer ◽  
Volker Derdau ◽  
María Mendez ◽  
Christoph Pöverlein ◽  
Olga Garcia Mancheno
Keyword(s):  
Natural Products ◽  
Visible Light ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Functional Group ◽  
Reaction Conditions ◽  
Site Selectivity ◽  
Wide Range ◽  
High Yields ◽  
Therapeutic Compounds

Abstract Visible light mediated late-stage functionalization is a rising field in synthetic and medicinal chemistry, allowing the fast and diversified modification of valuable, potentially therapeutic compounds such as peptides. However, there are relatively few mild methodologies for the C(sp3)-H functionalization of complex peptides. Herein, we report a visible light mediated photocatalytic protocol for the benzylic C-H modification of tyrosine and related C-H bonds. The embraced radical-cation/deprotonation strategy enables an incorporation of a wide range of valuable functional groups in high yields and chemoselectivity. The mild reaction conditions, site-selectivity and high functional group tolerance was highlighted by the functionalization of complex peptides, drugs and natural products, providing a promising synthetic platform in medicinal chemistry.

scholarly journals Double catalytic effect of (PhNH3)2CuCl4 in a novel, highly efficient synthesis of 2-oxo and thioxo-1,2,3,4-tetra-hydopyrimidines

2015 ◽  
Vol 80 (5) ◽  
pp. 595-604 ◽  
Author(s):  
Nenad Jankovic ◽  
Zorica Bugarcic ◽  
Svetlana Markovic
Keyword(s):  
Catalytic Effect ◽  
Biginelli Reaction ◽  
Aromatic Aldehydes ◽  
Homogeneous Catalyst ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Experimental Conditions ◽  
Complex Salts ◽  
Key Steps ◽  
Work Up

An innovative route for the construction of 2-oxo and thioxo-1,2,3,4-tetrahydropyrimidines was delineated through a multicomponent reaction under Biginelli conditions, starting from different aromatic aldehydes, ?-ketoesters and urea or thiourea. Proper choice of copper complex (PhNH3)2CuCl4, as a novel homogeneous catalyst, enables facile, efficient, and inexpensive reaction under mild experimental conditions. Moreover, we present the first application of this complex salts in organic synthesis ever. The obtained products are of high purity, and can be easily isolated from the reaction mixture in good to excellent yields. Also, compared to the classical Biginelli reaction conditions, the present method has the advantages in higher yields and experimental and work-up simplicity. To illustrate the joint catalytic action of the Cu2+ and phenylammonium ions, two key steps of Biginelli reaction were examined using the M06 functional.

Highly Enantioselective Michael Addition of Cyclic Diketones to β,γ-Unsaturated α-Keto Esters Catalyzed by Squaramide Organocatalyst

Synthesis ◽  
2022 ◽  
Author(s):  
Zhi-Wei Ma ◽  
Chuan-Chuan Wang ◽  
Quan-Jian Lv ◽  
Xiao-Pei Chen ◽  
Ai-Qin Li ◽  
...  
Keyword(s):  
Michael Addition ◽  
Large Scale ◽  
Catalyst System ◽  
Catalyst Loading ◽  
Reaction Conditions ◽  
Keto Esters ◽  
Bicyclic Compounds ◽  
Asymmetric Michael Addition ◽  
High Yields ◽  
Low Catalyst Loading

AbstractA new tertiary amine-squaramide organocatalyst has been developed and applied to the asymmetric Michael addition of cyclic diketones to β,γ-unsaturated α-keto esters. The catalyst system performed well with a low catalyst loading of 1 mol% under mild reaction conditions. A series of synthetically and pharmaceutically useful chiral bicyclic compounds were obtained in high yields (up to 97%) with excellent enantioselectivities (up to 99 % ee). Furthermore, this catalytic system can be used efficiently in large-scale reactions with the yields and enantioselectivities being maintained.

scholarly journals A Simple and Green Procedure for the Synthesis of 5-Arylidenerhodanines Catalyzed by Diammonium Hydrogen Phosphate in Water

2013 ◽  
Vol 2013 ◽  
pp. 1-4
Author(s):  
Liangliang Han ◽  
Tao Wu ◽  
Zhongqiang Zhou
Keyword(s):  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Hydrogen Phosphate ◽  
Reaction Conditions ◽  
Efficient Procedure ◽  
Diammonium Hydrogen Phosphate ◽  
High Yields ◽  
Green Procedure ◽  
Work Up ◽  
Diammonium Hydrogen

A simple and efficient procedure for the synthesis of 5-arylidenerhodanines by condensation of aromatic aldehydes with rhodanine in water using diammonium hydrogen phosphate as catalyst is described. The procedure offers several advantages including environmentally friendly, mild reaction conditions, short reaction times, high yields, and simple experimental and work-up procedures.

One Pot Synthesis of 6-(4-carboxy-3-methyl-2-phenylquinolin-6-ylsulfonyl)-3-methyl-2-phenylquinoline-4-carboxylic Acids from Dapsone and α-ketobutyric Acid by a Doebner Reaction

2016 ◽  
Vol 40 (12) ◽  
pp. 715-717 ◽  
Author(s):  
Negar Moshref Javadi ◽  
Javad Azizian
Keyword(s):  
Biological Activity ◽  
Carboxylic Acids ◽  
Anticancer Agents ◽  
Spectroscopic Data ◽  
Aromatic Aldehydes ◽  
Reaction Conditions ◽  
One Pot ◽  
Promising Alternative ◽  
Elemental Analyses ◽  
Operational Simplicity

A series of new 6-(4-carboxy-3-methyl-2-phenylquinolin-6-ylsulfonyl)-3-methyl-2-phenylquinoline-4-carboxylic acids were synthesised by a one-pot reaction of dapsone, α-ketobutyric acid, and aromatic aldehydes in the presence of CuBr2 as a catalyst. Operational simplicity, mild reaction conditions, and eco-friendly procedure make this novel protocol a promising alternative for the preparation of quinoline-4-caboxylic acid derivatives. The structures of the products were established by elemental analyses and spectroscopic data. The biological activity of the new sulfone dimers was evaluated as having the potential for use as anticancer agents.

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