scholarly journals One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation

2021 ◽  
Vol 8 ◽  
Author(s):  
Fa-Jie Chen ◽  
Zhenguo Hua ◽  
Jianhui Chen ◽  
Jiajia Chen ◽  
Daesung Lee ◽  
...  
Keyword(s):  
Efficient Method ◽  
Room Temperature ◽  
Copper Catalyst ◽  
High Yield ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Acid Chlorides ◽  
Triflic Acid ◽  
One Pot

Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-β-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity.

One-pot Synthesis of Pyrazolone Sulfones by Iodine-catalyzed Sulfenylation of Pyrazolones with Aryl Sulfonyl Hydrazides Followed by Oxidation in Water

2018 ◽  
Vol 15 (3) ◽  
pp. 380-387
Author(s):  
Xia Zhao ◽  
Xiaoyu Lu ◽  
Lipeng Zhang ◽  
Tianjiao Li ◽  
Kui Lu
Keyword(s):  
Double Bond ◽  
Efficient Method ◽  
Room Temperature ◽  
Sulfonyl Chloride ◽  
Antibacterial Activities ◽  
Oxidation Reactions ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray ◽  
Amide Form

Aim and Objective: Pyrazolone sulfones have been reported to exhibit herbicidal and antibacterial activities. In spite of their good bioactivities, only a few methods have been developed to prepare pyrazolone sulfones. However, the substrate scope of these methods is limited. Moreover, the direct sulfonylation of pyrazolone by aryl sulfonyl chloride failed to give pyrazolone sulfones. Thus, developing a more efficient method to synthesize pyrazolone sulfones is very important. Materials and Method: Pyrazolone, aryl sulphonyl hydrazide, iodine, p-toluenesulphonic acid and water were mixed in a sealed tube, which was heated to 100°C for 12 hours. The mixture was cooled to 0°C and m-CPBA was added in batches. The mixture was allowed to stir for 30 min at room temperature. The crude product was purified by silica gel column chromatography to afford sulfuryl pyrazolone. Results: In all cases, the sulfenylation products were formed smoothly under the optimized reaction conditions, and were then oxidized to the corresponding sulfones in good yields by 3-chloroperoxybenzoic acid (m-CPBA) in water. Single crystal X-ray analysis of pyrazolone sulfone 4aa showed that the major tautomer of pyrazolone sulfones was the amide form instead of the enol form observed for pyrazolone thioethers. Moreover, the C=N double bond isomerized to form an α,β-unsaturated C=C double bond. Conclusion: An efficient method to synthesize pyrazolone thioethers by iodine-catalyzed sulfenylation of pyrazolones with aryl sulfonyl hydrazides in water was developed. Moreover, this method was employed to synthesize pyrazolone sulfones in one-pot by subsequent sulfenylation and oxidation reactions.

A facile one pot route for the synthesis of imide tethered peptidomimetics

2016 ◽  
Vol 14 (2) ◽  
pp. 556-563 ◽  
Author(s):  
Veladi Panduranga ◽  
Girish Prabhu ◽  
Roopesh Kumar ◽  
Basavaprabhu Basavaprabhu ◽  
Vommina V. Sureshbabu
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Efficient Method ◽  
One Pot ◽  
Protected Amino Acid

A simple and efficient method for the synthesis of N,N’-orthogonally protected imide tethered peptidomimetics is presented. The imide peptidomimetics were synthesized by coupling the in situ generated selenocarboxylate of Nα-protected amino acids with Nα-protected amino acid azides in good yields.

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽  
2022 ◽  
Author(s):  
Dishu Zeng ◽  
Tianbao Yang ◽  
Niu Tang ◽  
Wei Deng ◽  
Jiannan Xiang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Organic Synthesis ◽  
Efficient Method ◽  
Building Block ◽  
Room Temperature ◽  
Uv Light ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Plausible Mechanism ◽  
High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

scholarly journals Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation

2017 ◽  
Vol 67 (3) ◽  
pp. 309-324 ◽  
Author(s):  
Nadjet Rezki ◽  
Mohamed Reda Aouad
Keyword(s):  
Antimicrobial Activity ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
One Pot ◽  
Alkyl Aryl ◽  
Antimicrobial Evaluation ◽  
Ultrasound Assisted ◽  
Click Synthesis

AbstractThe present study describes an efficient and ecofriendly, ultrasound, one-pot click cycloaddition approach for the construction of a novel series of 1,4-disubstituted-1,2,3-triazoles tethered with fluorinated 1,2,4-triazole-benzothiazole molecular conjugates. It involved three-component condensation of the appropriate bromoacetamide benzothiazole, sodium azide and 4-alkyl/aryl-5-(2-fluorophenyl)-3-(prop-2-ynylthio)-1,2,4-triazoles4a-ethrough a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction. This approach involvesin situgeneration of azidoacetamide benzothiazole, followed by condensation with terminal alkynes in the presence of CuSO4/Na-ascorbate in aqueous DMSO under both conventional and ultrasound conditions. Some of the designed 1,2,3-triazole conjugates6a-owere recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains.

An efficient multicomponent, one-pot synthesis of Betti bases catalyzed by cerium (IV) ammonium nitrate (CAN) at ambient temperature

2016 ◽  
Vol 5 (4) ◽  
Author(s):  
Ramadan Ahmed Mekheimer ◽  
Abdullah Mohamed Asiri ◽  
Afaf Mohamed Abdel Hameed ◽  
Reham R. Awed ◽  
Kamal Usef Sadek
Keyword(s):  
Ambient Temperature ◽  
Environmental Pollution ◽  
Ammonium Nitrate ◽  
Room Temperature ◽  
Catalytic Amount ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Work Up ◽  
Cerium Iv Ammonium Nitrate

AbstractStarting from readily available 2-naphthol, aldehydes, aryl and alkylamines, a variety of Betti bases were efficiently synthesized utilizing a catalytic amount of cerium (IV) ammonium nitrate (CAN) at room temperature. This protocol has advantages of high yield, mild reaction conditions, no environmental pollution, diversity of reactants and simple work up procedure.

One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling–intramolecular cyclization

2019 ◽  
Vol 9 (22) ◽  
pp. 6471-6481 ◽  
Author(s):  
Narasimha Swamy Thirukovela ◽  
Ramesh Balaboina ◽  
Vinayak Botla ◽  
Ravinder Vadde ◽  
Sreekantha Babu Jonnalagadda ◽  
...  
Keyword(s):  
Intramolecular Cyclization ◽  
Pd Nanoparticles ◽  
Environmentally Benign ◽  
Water Medium ◽  
Sonogashira Coupling ◽  
One Pot ◽  
Peg 400 ◽  
Sequential Coupling ◽  
Substituted Pyrazoles

Catalyst efficacy of in situ generated Pd-nanoparticles in the regioselective one-pot synthesis of substituted pyrazoles and isoxazoles via sequential coupling-cyclization methodology in environmentally benign medium is described.

scholarly journals Difunctionalization of alkenes with iodine and tert-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(tert-butylperoxy)-2-iodoethanes

2017 ◽  
Vol 13 ◽  
pp. 2023-2027 ◽  
Author(s):  
Hao Wang ◽  
Cui Chen ◽  
Weibing Liu ◽  
Zhibo Zhu
Keyword(s):  
Room Temperature ◽  
Synthetic Methods ◽  
Chemical Modifications ◽  
One Pot ◽  
Butyl Hydroperoxide ◽  
Radical Intermediates ◽  
Mild Conditions ◽  
Tert Butyl Hydroperoxide ◽  
Potential Applications

We developed a direct vicinal difunctionalization of alkenes with iodine and TBHP at room temperature. This iodination and peroxidation in a one-pot synthesis produces 1-(tert-butylperoxy)-2-iodoethanes, which are inaccessible through conventional synthetic methods. This method generates multiple radical intermediates in situ and has excellent regioselectivity, a broad substrate scope and mild conditions. The iodine and peroxide groups of 1-(tert-butylperoxy)-2-iodoethanes have several potential applications and allow further chemical modifications, enabling the preparation of synthetically valuable molecules.

Controllable Synthesis of Functional Polyaniline Nanotubes via a Complex Template

2015 ◽  
Vol 1120-1121 ◽  
pp. 220-224
Author(s):  
Ying Wang ◽  
Dong Hao Sun ◽  
Yan Feng Guo
Keyword(s):  
Electric Conductivity ◽  
Room Temperature ◽  
In Situ Polymerization ◽  
High Yield ◽  
Controllable Synthesis ◽  
Order Of Magnitude ◽  
Uv Visible ◽  
Acid Orange Ii ◽  
High Electric Conductivity

Functional Polyaniline (PANI) nanotubes are easily synthesized in high yield by an in situ polymerization using a fibrillar complex of acid orange II (AO II) and FeCl3as a template. During the process, the complex templates help direct the growth of fibrillar PANI on their surfaces, resulting in the formation of composite micro/nanofibers of PANI. After polymerization, by the post-treatment of removing templates in 1.0 M hydrochloric acid solution, PANI nanotubes with azo function and high electric conductivity of PANI are readily fabricated. The PANI nanotubes have about 150nm-300nm in diameter and several microns in length. At room temperature, the electric conductivity of PANI nanotubes is up to 10-1S/cm order of magnitude. The characterizations, including FTIR, UV-visible, XRD and TG, are presented.

One-Pot Transformation of Me3Si-/Ph2P(O)-Protected Ethynes to Unsymmetrical Arylethynes

2018 ◽  
Vol 42 (5) ◽  
pp. 271-273 ◽  
Author(s):  
Li-fen Peng ◽  
Jia-ying Lei ◽  
Li Wu ◽  
Zi-long Tang ◽  
Zhi-peng Luo ◽  
...  
Keyword(s):  
High Yield ◽  
Sonogashira Coupling ◽  
One Pot ◽  
Mild Conditions ◽  
Phenylene Ethynylenes

Me3Si-/Ph2P(O)-protected ethynes were successfully transformed to unsymmetrical arylethynes via a one-pot Ph2P(O)-deprotection/ [Pd(dppf)Cl2]-catalysed coupling and one-pot Me3Si-deprotection/Sonogashira coupling under mild conditions and in high yield. Unsymmetrical phenylethynes, unsymmetrical extended phenylene ethynylenes and unsymmetrical anthrylethynes were successfully synthesised in good to excellent yields.

Efficient Copper-Catalyzed Synthesis of Substituted Pyrazoles at Room Temperature

Synlett ◽  
2018 ◽  
Vol 29 (20) ◽  
pp. 2689-2692 ◽  
Author(s):  
Haifeng Wang ◽  
Xiangli Sun ◽  
Shuangling Zhang ◽  
Guanglu Liu ◽  
Chunjie Wang ◽  
...  
Keyword(s):  
Reaction Time ◽  
Catalytic System ◽  
Efficient Method ◽  
Room Temperature ◽  
Copper Catalyst ◽  
Condensation Reaction ◽  
Reaction Conditions ◽  
Short Reaction Time ◽  
Acid Catalyzed ◽  
Substituted Pyrazoles

An efficient method for the synthesis of pyrazoles through a copper-catalyzed condensation reaction has been developed. The new catalytic system not only maintained a broad substrate scope but was also active under acid-free reaction conditions, overcoming the conventional requirement for an acid-catalyzed system. Furthermore, the copper catalyst enabled this reaction to be performed at room temperature and in a short reaction time.

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