40524-62-7Relevant academic research and scientific papers
Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol
Biswal, Priyabrata,Samser, Shaikh,Meher, Sushanta Kumar,Chandrasekhar, Vadapalli,Venkatasubbaiah, Krishnan
supporting information, p. 413 - 419 (2021/11/01)
One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.
Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles
Chang, Weixing,Kong, Jingyang,Li, Jing,Liu, Lingyan,Wang, Hongkai,Zeng, Tianlong
supporting information, p. 4024 - 4032 (2021/07/12)
Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).
A new method for the synthesis of chalcone derivatives promoted by PPh3/I2under non-alkaline conditions
Xue, Kangsheng,Sun, Guoxiang,Zhang, Yanzhi,Chen, Xubing,Zhou, Yang,Hou, Jinjun,Long, Huali,Zhang, Zijia,Lei, Min,Wu, Wanying
supporting information, p. 625 - 634 (2020/11/23)
A straightforward and general method has been developed for the synthesis of chalcone derivatives by a Claisen-Schmidt reaction in the presence of PPh3/I2 in 1,4-dioxane under reflux temperatures. With the condensation of the aromatic ketone and aldehyde occurring at non-strongly alkaline conditions, our proposed method significantly expands the range of applicable substrates, especially for groups that are unstable under alkaline conditions.
Synthesis of pyrazolopyrimidine derivatives along with its biological activity including toxicity studies
Singh,Gousuddin, Mohammad,Khan, Huma
, p. 182 - 200 (2021/02/27)
Pyrazolopyrimidines and related fused heterocycles are of interest as potential bioactive molecules. The heterocyclic fusion of pyrimidine ring and pyrazole ring resulted in formation of pyrazolopyrimidines, the structural analogues of biogenic purine class, undoubtedly, has high significance in the field of pharmaceutical and biotechnological sciences with wide spectrum of biological activities and its several derivatives. Toxicity may be due to the accumulation in a specific organ/ tissue (e.g. bosentan), the co - administration of other drugs affecting ADMET (absorption, distribution, metabolism, elimination and toxicity) Cmax reaching off target IC50, or the high Cmax required for therapeutic effects. Assessing the relative drug efficacy and toxicity is important for medicinal chemists, pharmacologists, pharmacists, physicians. As multiple treatment options are available for many diseases, relative toxicity assessment is necessary. Difficulty in direct clinical trial comparisons forces network meta-analyses for estimating the relative toxicity. Therapeutic index (TI) assumes simplified linear relationships between receptor affinity, maximum unbound plasma drug concentration (Cmax) and toxicity. But high TI does not guarantee safety. For drugs metabolized by cytochrome P450 (CYP450),estimating TI based on target potencies alone is insufficient.
Organo-catalyzed Michael addition of 2-fluoro-2-arylacetonitriles
Chen, De-Yin,Song, Shuai,Chen, Ling-Yan,Ren, Xinfeng,Li, Ya
supporting information, (2021/03/01)
An efficient synthesis of a variety of 2-arylacetonitriles containing a fluorinated stereogenic center through organo-catalyzed Michael addition reaction of 2-fluoro-2-arylacetonitriles has been developed. This protocol uses a cheap organocatalyst (DBU) and has a broad substrate scope: α, β-unsaturated ketones, esters, nitriles and sulfones were all successfully reacted. Importantly, water proved to be a good solvent for this reaction.
Promising Non-cytotoxic Monosubstituted Chalcones to Target Monoamine Oxidase-B
Iacovino, Luca G.,Pinzi, Luca,Facchetti, Giorgio,Bortolini, Beatrice,Christodoulou, Michael S.,Binda, Claudia,Rastelli, Giulio,Rimoldi, Isabella,Passarella, Daniele,Di Paolo, Maria Luisa,Dalla Via, Lisa
supporting information, p. 1151 - 1158 (2021/06/30)
A library of monosubstituted chalcones (1-17) bearing electron-donating and electron-withdrawing groups on both aromatic rings were selected. The cell viability on human tumor cell lines was evaluated first. The compounds unable to induce detectable cytotoxicity (1, 13, and 14) were tested using the monoamine oxidase (MAO) activity assay. Interestingly, they inhibit MAO-B, acting as competitive inhibitors, with 13 and 14 showing the best profiles. In particular, 13 exhibited a potency higher than that of safinamide, taken as a reference. Docking studies and crystallographic analysis showed that in human MAO-B 13 binds with the halogen-substituted aromatic ring in the entrance cavity, similar to safinamide, whereas 14 is accommodated in the opposite way. The main conclusion of this cell biology, biochemistry, and structural study is to highlights 13 as a chalcone derivative that is worth consideration for the development of novel MAO-B-selective inhibitors for the treatment of neurodegenerative diseases.
Synthesis of Ketones by C?H Functionalization of Aldehydes with Boronic Acids under Transition-Metal-Free Conditions
Roscales, Silvia,Csáky, Aurelio G.
supporting information, p. 8728 - 8732 (2021/03/16)
A method for the synthesis of ketones from aldehydes and boronic acids via a transition-metal-free C?H functionalization reaction is reported. The method employs nitrosobenzene as a reagent to drive the simultaneous activation of the boronic acid as a boronate and the activation of the C?H bond of the aldehyde as an iminium species that triggers the key C?C bond-forming step via an intramolecular migration from boron to carbon. These findings constitute a practical, scalable, and operationally straightforward method for the synthesis of ketones.
Iridium and copper supported on silicon dioxide as chemoselective catalysts for dehydrogenation and borrowing hydrogen reactions
Zhu, Guanxin,Duan, Zheng-Chao,Zhu, Haiyan,Qi, Minghui,Wang, Dawei
, (2021/04/02)
High active ligand usually plays an important role during catalysis and synthesis chemistry. A new and efficient benzotriazole-pyridinyl-silane ligand (BPS) was designed, and the corresponding iridium and copper catalysts were synthesized and thoroughly characterized by means of EDS, TEM, and XPS. The resulting iridium composite revealed excellent catalytic activity for the reaction of tert-butanesulfinamide with benzyl alcohols, while copper catalyst could realize the synthesis of unsaturated carbonyl compounds through the reaction of benzyl alcohols with ketones. This provided an efficient method for selective synthesis of unsaturated carbonyl compounds from benzyl alcohols and ketones in high yields with good recovery performance.
A Convenient One-Pot Synthesis of Chalcones and Their Derivatives and Their Antimicrobial Activity
Salotra,Utreja,Sharma
, p. 2207 - 2211 (2021/02/09)
Abstract: A series of chalcones were synthesized by base-catalyzed Clasien-Schmidtcondensation of substituted benzaldehydes and substituted acetophenones at roomtemperature. The addition of hydrazine hydrate and hydroxylamine hydrochlorideacross the double bond of the obtained chalcones gave pyrazole and isoxazolederivatives, respectively. All the synthesized compounds were characterized by1H and 13C NMR andFT-IR spectroscopy and screened for their in vitro antimicrobial activityagainst two bacterial strains, Pseudomonasaeruginosa and Pseudomonasoryzihabitans using Ciprofloxacin as standard drug.1-(2-Methoxyphenyl)-3-phenylprop-2-en-1-one and1-(4-chlorophenyl)-3-phenylprop-2-en-1-one showed significant activity againstboth bacterial strains and hence proved to be potent antimicrobialagents.
Photoredox β-thiol-α-carbonylation of enones accompanied by unexpected Csp2-C(CO) bond cleavage
Du, Ding,Feng, Jie,Ma, Rui,Zhang, Beichen,Zhang, Kuili
supporting information, p. 7549 - 7553 (2020/10/13)
An olefinic difunctionalization method of enones was presented hereviaaerobic visible-light catalysis. A novel reactivity was showcased in conjunction with the selective Csp2-C(CO) bond activation of enones, which provided a convenient method for the preparation of various β-thiolated-α-functionalized compounds. Moreover, the preliminary investigation of the mechanism indicated that a β-peroxysulfide intermediate was formed under the promotion of visible light under an oxygen atmosphere, which finally induced the unexpected C-C bond cleavage.
