scholarly journals Expanding structural diversity in a library of disulfide macrocycles through in-situ imide hydrolysis

2022 ◽  
Vol 12 (1) ◽  
Author(s):  
Marcin Konopka ◽  
Artur R. Stefankiewicz

AbstractWe describe here an unorthodox approach to dynamic covalent chemistry in which the initially-unexpected in-situ hydrolysis of a bis-imide is employed to control the composition of a library of structurally diverse macrocycles. A single building block is used to generate a library of numerous disulfide-based architectures in a one-pot single-step process. The dual-stimuli method is based on simultaneous changes in pH and DMSO concentration to expand the structural diversity of the macrocyclic products. Mechanistic details of this complex process are investigated by the kinetics analysis. We delivered a facile strategy for the synthesis of water-soluble, multicomponent and dynamic macrocycles equipped with number of different functional groups, thus giving a prospect of their application in guest-driven phase transfer.

2021 ◽  
Author(s):  
Marcin Konopka ◽  
Artur R. Stefankiewicz

Abstract We describe here an unorthodox approach to dynamic covalent chemistry in which the initially-unexpected in-situ hydrolysis of a bis-imide component is used to control the composition of a library of structurally diverse macrocycles. The dual-stimuli method is based on simultaneous changes in pH and DMSO concentration to expand the diversity of the macrocyclic architectures.


2021 ◽  
Author(s):  
Rafał Kusy ◽  
Karol Grela

Herein, we present (<i>Z</i>)-selective transfer semihydrogenation of alkynes based on in situ generated CuNPs in the presence of hydrogen donors, such as ammonia-borane and a protic solvent. This environmentally-friendly method is characterized by operational simplicity combined with high stereo- and chemoselectivity and functional group compatibility. Auto-oxidation of CuNPs after the semihydrogenation reaction is completed results in the formation of water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need of any special regeneration process. Formed NH<sub>4</sub>B(OR)<sub>4</sub> can be easily transformed back to ammonia-borane or to boric acid. In addition, one-pot tandem sequence involving Suzuki reaction followed by semihydrogenation was presented.<br>


Synthesis ◽  
2019 ◽  
Vol 51 (20) ◽  
pp. 3796-3804 ◽  
Author(s):  
Marine Rey ◽  
Stéphane Beaumont

A one-pot approach for the direct synthesis of substituted pyrazoles from isoxazoles is reported. The process involves isoxazole N–O bond cleavage mediated by a molybdenum complex, in situ hydrolysis of the resulting β-amino enone to the corresponding 1,3-diketone, followed by pyrazole formation in the presence of hydrazine or substituted hydrazine. Good to excellent yields and regioselectivities are obtained with nonsymmetric isoxazoles. By using readily available starting materials, a wide range of substituted pyrazoles may be synthesized by this method.


2015 ◽  
Vol 51 (57) ◽  
pp. 11398-11400 ◽  
Author(s):  
Jingfang Yu ◽  
Lichen Xiang ◽  
Benjamin R. Martin ◽  
Abraham Clearfield ◽  
Luyi Sun

A single step one-pot in situ synthesis method was developed to directly grow layered intercalation compounds. This methodology is expected to be applicable to a wide range of layered materials.


2016 ◽  
Vol 35 (1) ◽  
pp. 45
Author(s):  
Naoufel Ben Hamadi ◽  
Ahlem Guesmi ◽  
Wided Nouira

Cycloaddition of the diazoalkanes to electron-deficient olefins (in situ) affords polysubstituted cyclopropanes in high yields (up to 85%). Deprotection of the ketal protecting group provided water-soluble cyclopropane-bearing carbohydrate in good yields. Antimicrobial activity screening of the synthesized compounds 8 and 9, utilizing a variety of Gram-positive (Staphylococcus aureus and Enterococcus fecalis), Gram-negative bacteria (Escherichia coli and Klebsiella pneumoniae) and yeast (Candida albicans), exhibited that all the prepared analogues acquire promising activities against both Gram-positive and Gram-negative bacteria especially compounds 9b and 9c (antimicrobial active agents against Gram-negative bacteria).


Organics ◽  
2021 ◽  
Vol 2 (4) ◽  
pp. 404-414
Author(s):  
Tomas Opsomer ◽  
Kaat Valkeneers ◽  
Ana Ratković ◽  
Wim Dehaen

1,2,3-Triazole-4-carbaldehydes are useful synthetic intermediates which may play an important role in the discovery of novel applications of the 1,2,3-triazole moiety. In this work, a one-step multigram scale synthesis of 4-formyl-1-(4-nitrophenyl)-1H-1,2,3-triazole (FNPT) as a preferred reagent for the synthesis of 1-alkyl-4-formyltriazoles is described, making use of the commercially available 3-dimethylaminoacrolein and 4-nitrophenyl azide. Next, the earlier reported reaction of FNPT with alkylamines is further explored, and for hexylamine, the one-pot sequential cycloaddition and Cornforth rearrangement is demonstrated. In addition, a useful protocol for the in situ diazotization of 4-nitroaniline is provided. This facilitated the complete hydrolysis of rearranged 4-iminomethyl-1,2,3-triazoles and allowed for the recycling of 4-nitrophenyl azide.


Polymers ◽  
2020 ◽  
Vol 12 (8) ◽  
pp. 1807
Author(s):  
Sri Mulyati ◽  
Syawaliah Muchtar ◽  
Nasrul Arahman ◽  
Friska Meirisa ◽  
Yanna Syamsuddin ◽  
...  

This paper reports the fabrication of polyethersulfone membranes via in situ hydrogen peroxide-assisted polymerization of dopamine. The dopamine and hydrogen peroxide were introduced into the dope solution where the polymerization occurred, resulting in a single-step additive formation during membrane fabrication. The effectivity of modification was evaluated through characterizations of the resulting membranes in terms of chemical functional groups, surface morphology, porosity, contact angle, mechanical strength and filtration of humic acid solution. The results confirm that the polydopamine was formed during the dope solution mixing through peroxide-assisted polymerization as proven by the appearance of peaks associated OH and NH groups in the resulting membranes. The presence of polydopamine residual in the membrane matric enhances the pore properties in terms of size and porosity (by a factor of 10), and by lowering the hydrophilicity (from 69° to 53°) which leads to enhanced filtration flux of up to 217 L/m2 h. The presence of the residual polydopamine also enhances membrane surface hydrophilicity which improve the antifouling properties as shown from the flux recovery ratio of > 80%.


2021 ◽  
Author(s):  
Kritika Laxmikeshav ◽  
Akash P Sakla ◽  
Stephy Elza John ◽  
Shankaraiah Nagula

A facile and proficient dithiocarbamation of imidazo[1,2-a]pyridines and other imidazoheterocycles with in situ generated dithiocarbamates is established using a water-soluble, stable copper(I) catalyst and molecular oxygen under microwave conditions. The...


2016 ◽  
Vol 2016 ◽  
pp. 1-10
Author(s):  
Lingzhi Zhao ◽  
Liu Zhao ◽  
Yanqing Miao ◽  
Chunye Liu ◽  
Chenxiao Zhang

The detection of pyrophosphatase (PPase) activity is of great significance in diagnosing diseases and understanding the function of PPase-related biological events. This study constructed a turn off-on-off fluorescent system for PPase activity assay based on PPase-regulated competitive coordination of Cu2+between a water-soluble fluorescent probe 6,7-dihydroxycoumarin (DHC) and pyrophosphate (PPi). The probe DHC can coordinate with Cu2+and consequently display on-off type fluorescence response. Furthermore, the in situ formed nonfluorescent Cu2+-DHC complex can act as an effective off-on type fluorescent probe for sensing PPi due to the higher coordination reactivity between Cu2+and PPi than that between Cu2+and DHC. The subsequent addition of PPase to the mixture containing Cu2+, DHC, and PPi leads to the fluorescence requenching of the system again (an off state) because PPase catalyzes the hydrolysis of PPi into orthophosphate in the reaction system. Under the optimum conditions, the decrease of the fluorescence intensity of DHC-Cu2+-PPi system was linear with the increase of the PPase activity in the range from 0.1 to 0.3 U. The detection limit was down to 0.028 U PPase (S/N=3). Moreover, the as-established system was also applied to evaluate PPase inhibitor. This study offers a simple yet effective method for the detection of PPase activity.


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