Discovery of Oxolane-2-carbonyl chloride

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A “bottom-up” approach to process development: Application of physicochemical properties of reaction products toward the development of direct-drop processes

The “bottom-up” approach to development of direct-drop processes is a powerful, yet simple, strategy that every process chemist should consider for the development of efficient, cost-effective, and environmentally friendly processes. This approach is aided by a “parallel crystallization” technique, which allows for rapid identification of multiple solvent systems for the crystallization of the desired product using a minimal amount of material and solvent. This “bottom-up” approach is illustrated by several examples where the desired product is crystallized directly from the reaction mixture.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Design and synthesis of aminothiazole based Hepatitis B Virus (HBV) capsid inhibitors

The capsid assembly is an essential step for Hepatitis B Virus (HBV) life cycle and is an important target for anti-HBV drug development. In this report, we identified a hit compound with aminothiazole structure by the high throughput screening (HTS) which inhibited the interaction of HBV capsid protein within the cells. The structure hopping and SAR studies of the hit compound afforded compound 79 with potent anti-HBV replication activity and good basic drug-like properties. The working mechanism studies showed that compound 79 could bind to the similar binding site of known HBV capsid inhibitor with heteroaryldihydropyrimidine (HAP) scaffold, through similar hydrophobic interactions but with a different hydrogen bond. This compound exerted potent inhibitory effect upon HBV production, either in cell culture or in mice with no obvious acute toxicity. We propose that further development of this compound could lead to novel potent anti-HBV inhibitors that target HBV capsid assembly.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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A process for the preparation of the medicament kuikui zuo lin kind improved process (by machine translation)

The invention relates to a process for the preparation of the medicament kuikui zuo lin kind improved process, to provide a 2 – chloro – 4 – amino – 6, 7 – dimethoxy quinazoline as intermediate synthetic route, in particular comprising the following steps: acrylonitrile with the methylamine is mellow solution is amine reaction to obtain the intermediate (I); in triethylamine as acid benzyl chloride under conditions as protection basal into intermediate (II); the use of metal duplicate hydride reduction to produce intermediate (III); with the tetrahydrofuran chloride in the acylation reaction intermediate (IV); intermediate (IV) under the catalysis of palladium hydrogenolysis reaction occurs with the formic acid amine to obtain the intermediate (V); the final with 2 – chloro – 4 – amino – 6, 7 – dimethoxy quinazoline generate condensation reaction, to obtain the drug kuikui zuo lin kind alfuzosin hydrochloride (VI). Compared with the other production process, the present invention provides a simple operation, safety, easy control of reaction conditions, low energy consumption, yield stable production process, and has good prospects for industrial application. (by machine translation)

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Tetrahydrofuran – Wikipedia,
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Synthesis, structure and pyrolysis of stabilised phosphonium ylides containing saturated oxygen heterocycles

A range of twelve stabilised phosphonium ylides containing tetrahydrofuran, tetrahydropyran or 2,2-dimethyl-1,3-dioxolane rings have been prepared and fully characterised, including one X-ray structure determination of each type. The X-ray structures confirm the P=C and C=O functions to be syn and all the compounds undergo thermal extrusion of Ph3PO to give the corresponding alkynes. In some cases there is also competing loss of Ph3P to give different carbene-derived products and evidence has been obtained for the generation of 2-phenyloxete in this way. Raising the pyrolysis temperature leads in several cases to new secondary reactions of the alkyne products involving a sequence of alkyne to vinylidene isomerisation, intramolecular CH insertion, and retro Diels Alder reaction.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Design and Biological Evaluation of Furan/Pyrrole/Thiophene-2-carboxamide Derivatives as Efficient DNA GyraseB Inhibitors of Staphylococcus aureus

DNA topoisomerases are well-validated targets in micro-organisms. DNA gyraseB is one of the most important enzymes among them as per their clinical importance. In earlier study, a novel lead 4-((4-(furan-2-carboxamido)phenyl)amino)-4-oxobutanoic acid was identified as inhibitor against DNA gyraseB with an IC50 of 12.88 ¡À 1.39 mum. Subsequently, analogues of this lead were developed and evaluated through in vitro assays and in vivo studies. Among the 24 analogues, compound 22 was found to be the top hit with an improved DNA gyraseB activity of 5.35 ¡À 0.61 mum, and the binding affinity of this compound was further ascertained biophysically through differential scanning fluorimetry. The most potent ligand did not show any signs of cardiotoxicity in zebra fish ether-ago-go-related gene, ascertaining the safety profile of this series a breakthrough among the previously reported cardiotoxic gyraseB inhibitors.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Pyridine-3-propanoic acids: Discovery of dual PPARalpha/gamma agonists as antidiabetic agents

A series of novel pyridine-3-propanoic acids was synthesized. A structure-activity relationship study of these compounds led to the identification of potent dual PPARalpha/gamma agonists with varied isoform selectivity. Based on the results of efficacy studies in diabetic (db/db) mice, and the desired pharmacokinetic parameters, compounds (S)-14 and (S)-19 were selected for further profiling.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Related Products of 52449-98-6, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 52449-98-6, molcular formula is C5H7ClO2, introducing its new discovery.

Safe, selective, and high-yielding synthesis of acryloyl chloride in a continuous-flow system

Acid chlorides are an important class of compounds and their high reactivity and instability has prompted us to develop a straightforward procedure for their synthesis with ondemand and on-site synthesis possibilities. The focus of this report is acryloyl chloride, mainly important for the acrylate and polymer industry. A continuous-flow methodology was developed for the fast and selective synthesis of the otherwise highly unstable acryloyl chloride. Three routes were investigated in a microreactor setup and all three can potentially be used for its production. The methodology was further expanded to the synthesis of other unstable acid chlorides by both the thionyl chloride and the oxalyl chloride mediated processes. The most sustainable method was the oxalyl chloride mediated procedure under solvent-free conditions, in which nearequimolar amounts of carboxylic acid and oxalyl chloride were used in the presence of catalytic amounts of DMF at room temperature. Within 1 to 3 min, nearly full conversions into the acid chlorides were achieved.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Staudinger reactions of unsymmetrical cyclic ketenes: A synthetically useful approach to spiro beta-lactams and derivatives. Reaction mechanism and theoretical studies

An efficient and operationally simple synthesis of tetrahydrofuran-derived spiro-beta-lactams using the ketene-imine cycloaddition route is described. Also the preparation of spiro-N-sulfonyl-beta-lactam derivatives, which are analogs of monobactams, is reported. As far as we know, this is the first time that an unsymmetrical cyclic ketene is used in a Staudinger-type reaction. The experimental evidence suggests the involvement of a ketene derived from the acyl chloride precursor in the reaction. High-level ab initio calculations have been performed in order to get insight into the electronic effects controlling the stereochemical outcome of the reactions.

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THIAZOLOPYRIMIDINONE DERIVATIVES AS PI3 KINASE INHIBITORS

This invention relates to the use of thiazolopyrimidinone derivatives for the modulation, notably the inhibition of the activity or function of the phosphoinositide 3? OH kinase family (hereinafter PI3 kinases), suitably, PI3Kalpha, PI3Kdelta, PI3Kbeta, and/or PI3Kgamma. Suitably, the present invention relates to the use of thiazolopyrimidinones in the treatment of one or more disease states selected from: autoimmune disorders, inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, allergy, asthma, pancreatitis, multiorgan failure, kidney diseases, platelet aggregation, cancer, sperm motility, transplantation rejection, graft rejection and lung injuries. More suitably, the present invention relates to PI3Kbeta selective thiazolopyrimidinones compounds for treating cancer

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Tetrahydrofuran – Wikipedia,
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New insights into the torquoselectivity of the staudinger reaction

To understand the torquoselectivity and the electronic effects of the Staudinger reaction, a study using a combination of experiments and DFT calculations has been conducted for the reactions of an unsymmetric cyclicketene and cyclic imines with different electronic properties. The pred ominant formation of the donor-in beta-lactams, the torquoelectronically disfavored products, was observed for the first time. The Hammett analyses reveal a close relationship between the donor-out/donor-in productratio and the electronic nature of the imines. The kinetic competition experiments and DFT calculations indicate that the two-step Staudinger r eaction shows different rate-determining steps in the donor-in and donor-out pathways. Our investigations reveal that the torquoelectronic control in the Staudinger reaction is quite different from that in the ring-opening reaction of cyclobutene derivatives. The diastereoselectivity of the Staudinger reaction involving an unsymmetric disubstituted ketene cannot be simply rationalized or predicted by the torquoelectronic model.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem