- Studies in sulfur-nitrogen nucleophilicity
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As part of a study of nitrogen vs sulfur nucleophiles, the behavior of methylation products from dimethyl-(2-methylthioethyl)amine CH3SCH2CH2N(CH3)2 1 is described. Of the 2 potential products (a sulf
- Caserio, Marjorie C.,Kim, Jhong K.
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Read Online
- Design, synthesis, and biological evaluation of 2,6,7-substituted pyrrolo[2,3-d]pyrimidines as cyclin dependent kinase inhibitor in pancreatic cancer cells
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Pancreatic cancer is a highly malignant tumor, and more effective treatment is urgently needed to lengthen the life of patients. In this paper a class of new 2,6,7-substituted pyrrolo[2,3-d]pyrimidine derivatives of CDK 4/6 inhibitor ribociclib (1) was de
- Shi, Xingpeng,Quan, Yanni,Wang, Yixuan,Wang, Ying,Li, Yanping
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supporting information
(2020/12/29)
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- Palladium-Catalyzed β-C(sp3)-H Arylation of Aliphatic Ketones Enabled by a Transient Directing Group
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The direct arylation of aliphatic ketones has been developed via Pd-catalyzed β-C(sp3)-H bond functionalization with 2-(aminooxy)-N,N-dimethylacetamide as a novel transient directing group (TDG), which showed remarkable directing ability to generate arylated products in moderate to good yields. Furthermore, the reaction can tolerate abundant substrate of ketones and aryl iodides. This study expands the scope of applications for TDGs.
- Wang, Yangyang,Wu, Gaorong,Xu, Xiaobo,Pang, Binghan,Liao, Shaowen,Ji, Yafei
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p. 7296 - 7303
(2021/05/29)
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- Novel selective ido1 inhibitors with isoxazolo[5,4-d]pyrimidin-4(5h)-one scaffold
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Indoleamine 2,3-dioxygenase 1 (IDO1) is a promising target in immunomodulation of several pathological conditions, especially cancers. Here we present the synthesis of a series of IDO1 inhibitors with the novel isoxazolo[5,4-d]pyrimidin-4(5H)-one scaffold. A focused library was prepared using a 6-or 7-step synthetic procedure to allow a systematic investigation of the structure-activity relationships of the described scaffold. Chemistry-driven modifications lead us to the discovery of our best-in-class inhibitors possessing p-trifluoromethyl (23), p-cyclohexyl (32), or p-methoxycarbonyl (20, 39) substituted aniline moieties with IC50 values in the low micromolar range. In addition to hIDO1, compounds were tested for their inhibition of indoleamine 2,3-dioxygenase 2 and tryptophan dioxygenase, and found to be selective for hIDO1. Our results thus demon-strate a successful study on IDO1-selective isoxazolo[5,4-d]pyrimidin-4(5H)-one inhibitors, defining promising chemical probes with a novel scaffold for further development of potent small-molecule immunomodulators.
- ?vajger, Urban,Bratkovi?, Toma?,Dol?ak, Ana,Gobec, Stanislav,Mlinari?, Larisa,Ogorevc, Eva,Sova, Matej
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- Quinazoline derivative and application thereof as antitumor drug
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The invention belongs to the technical field of medicinal chemistry, and relates to a quinazoline derivative shown as a general formula (I), physiologically acceptable salt formed by the quinazoline derivative and inorganic or organic acid, a pharmaceutical composition containing the quinazoline derivative and the physiologically acceptable salt, and application of the quinazoline derivative and the pharmaceutical composition to preparation of drugs for treating tumor diseases, particularly drugs for treating abnormal EGFR family diseases. The compound has pharmacological properties with important values, and especially has an inhibition effect on signal transduction caused by tyrosine kinase.
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Paragraph 0073-0076
(2020/08/22)
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- Design, synthesis and evaluation of new indolylpyrimidylpiperazines for gastrointestinal cancer therapy
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Human A3 adenosine receptor hA3AR has been implicated in gastrointestinal cancer, where its cellular expression has been found increased, thus suggesting its potential as a molecular target for novel anticancer compounds. Observation
- Tan, Aaron,Babak, Maria V.,Venkatesan, Gopalakrishnan,Lim, Clarissa,Klotz, Karl-Norbert,Herr, Deron Raymond,Cheong, Siew Lee,Federico, Stephanie,Spalluto, Giampiero,Ong, Wei-Yi,Chen, Yu Zong,Loo, Jason Siau Ee,Pastori, Giorgia
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- Intramolecular carbene C-H insertion reactions of 2-diazo-2-sulfamoylacetamides
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The intramolecular C-H insertions of carbenes derived from 2-diazo-2-sulfamoylacetamides were studied. 2-Diazo-2-sulfamoylacetamides were first prepared from chloroacetyl chloride and secondary amines through acylation followed by sequential treatments with sodium sulfite, phosphorus oxychloride, secondary amines, and 4-nitrobenzenesulfonyl azide. The results indicate that: (1) 2-diazo-N,N-dimethyl-2-(N,N-diphenylsulfamoyl)acetamide can take the formal aromatic 1,5-C-H insertion in its N-phenylsulfonamide moiety to afford the corresponding 1,3-dihydrobenzo[c]isothiazole-3-carboxamide 2,2-dioxide derivative; (2) no aliphatic C-H insertions occur for 2-diazo-2-(N,N-dialkylsulfamoyl)acetamides; and (3) for 2-diazo-N-phenyl-2-(N-phenylsulfamoyl)acetamides, the formal aromatic 1,5-C-H insertion in the N-phenylacetamide moiety is favorable to afford the corresponding 3-sulfamoylindolin-2-one derivatives as sole or major products. The intramolecular competitive aromatic 1,5-C-H insertion reactions of 2-diazo-2-sulfamoylacetamides with aryl groups on both amide and sulfonamide groups reveal that the N-aryl substituents on acetamide are more active than those on sulfonamide. The chemoselectivity is controlled by electronic effect of the aryl group.
- Que, Chuqiang,Huang, Peipei,Yang, Zhanhui,Chen, Ning,Xu, Jiaxi
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- DRUGS TO TREAT OCULAR DISORDERS
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The present invention provides new prodrugs of therapeutically active loop diuretics, including oligomeric prodrugs, and compositions to treat medical disorders, for example, ocular disorders such as glaucoma, a disorder or abnormality related to an increase in intraocular pressure (IOP), a disorder requiring neuroprotection, age-related macular degeneration, or diabetic retinopathy.
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Page/Page column 223
(2019/11/12)
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- Design and synthesis of aminothiazolyl norfloxacin analogues as potential antimicrobial agents and their biological evaluation
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A series of aminothiazolyl norfloxacin analogues as a new type of potential antimicrobial agents were synthesized and screened for their antimicrobial activities. Most of the prepared compounds exhibited excellent inhibitory efficiencies. Especially, norfloxacin analogue II-c displayed superior antimicrobial activities against K. pneumoniae and C. albicans with MIC values of 0.005 and 0.010 mM to reference drugs, respectively. This compound not only showed broad antimicrobial spectrum, rapid bactericidal efficacy and strong enzymes inhibitory potency including DNA gyrase and chitin synthase (CHS), low toxicity against mammalian cells and no obvious propensity to trigger the development of bacterial resistance, but also exerted efficient membrane permeability, and could effectively intercalate into K. pneumoniae DNA to form a steady supramolecular complex, which might block DNA replication to exhibit their powerful antimicrobial activity. Quantum chemical studies were also performed to explain the high antimicrobial activities. Molecular docking showed that compound II-c could bind with gyrase–DNA and topoisomerase IV–DNA through hydrogen bonds and π-π stacking.
- Wang, Liang-Liang,Battini, Narsaiah,Bheemanaboina, Rammohan R.Yadav,Zhang, Shao-Lin,Zhou, Cheng-He
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p. 105 - 123
(2019/02/15)
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- Design and Synthesis of New Aryloxy-linked Dimeric 1,2,3-Triazoles via Click Chemistry Approach: Biological Evaluation and Molecular Docking Study
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A quest for more potent new antitubercular agents has prompted to design and synthesize aryloxy-linked dimeric 1,2,3-triazoles (4a–j), from azides (2a-e) and bis(prop-2-yn-1-yloxy)benzene (3a–b) on 1,3-dipolar cycloaddition reaction via copper (I)-catalyzed click chemistry approach with good to better yields. The titled compounds (4a–j) were designed using molecular hybridization approach by assembling various bioactive pharmacophoric fragments in a single molecular framework. All the synthesized compounds have been screened for their in vitro antitubercular, antifungal, and antioxidant activities against their respective strains. Among them, 4h and 4i show the highest antifungal activity, whereas compounds 4h, 4i, and 4j have revealed promising antitubercular activity against their respective strains. In addition to this, most of the synthesized compounds were found as potent antifungal and antioxidant agents. A significant network of bonded and non-bonded interactions stabilized these molecules into the active site of fungal CYP51 that is realized from the obtained well-placed docking poses and the associated thermodynamic interactions with the enzyme. The synthesized compounds have also been analyzed for absorption, distribution, metabolism, and excretion properties.
- Deshmukh, Tejshri R.,Khare, Smita P.,Krishna, Vagolu S.,Sriram, Dharmarajan,Sangshetti, Jaiprakash N.,Bhusnure, Omprakash,Khedkar, Vijay M.,Shingate, Bapurao B.
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p. 2144 - 2162
(2019/07/12)
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- Synthesis, bioevaluation and molecular docking study of new piperazine and amide linked dimeric 1,2,3-triazoles
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In search of more potent new antitubercular agents, a library of novel piperazine tethered dimeric 1,2,3-triazoles were designed by assembling 1,2,3-triazoles and piperazine in a single molecular architectural framework. The titled compounds (3a–m) were synthesized by 1,3-dipolar cycloaddition of 1,4-di(prop-2-yn-1-yl)piperazine (1) and various azides (2a–m) using click chemistry approach with good yields. All the synthesized compounds (3a–m) have been screened for their in vitro antitubercular, antifungal and antioxidant activities against their respective strains. Among them, 3b, 3d, and 3i have revealed promising antitubercular activity against Mycobacterium tuberculosis (Mtb) H37Rv with MIC 12.5 μg/mL. Molecular docking results provided well-clustered solutions to the mode of binding for these molecules into the active site of Mtb enoyl reductase (InhA). In addition to this, most of synthesized compounds were found to have potential antifungal as well as antioxidant activity.
- Deshmukh, Tejshri R.,Khare, Smita P.,Khedkar, Vijay M.,Krishna, Vagolu S.,Sangshetti, Jaiprakash N.,Shingate, Bapurao B.,Sriram, Dharmarajan
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supporting information
(2019/12/03)
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- Efficient α-chlorination of carbonyl containing compounds under basic conditions using methyl chlorosulfate
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An efficient method for the α-chlorination of ketones under basic conditions is described using methyl chlorosulfate. Its applicability for the chlorination of other functional groups has also been studied and it is equally useful for the synthesis of α-chloroesters and amides. Methyl chlorosulfate is described for the first time as a positive chlorine source. Some aldol reactions which occur during the chlorination of some substrates are also reported.
- Silva, Saúl,Maycock, Christopher D.
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supporting information
p. 1233 - 1238
(2018/02/27)
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- Structure–activity relationship investigation of coumarin–chalcone hybrids with diverse side-chains as acetylcholinesterase and butyrylcholinesterase inhibitors
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Chalcones containing tertiary amine side-chains have potent activity as acetylcholinesterase (AChE) inhibitors. However, the effects of the location of the tertiary amine groups as well as of other groups on AChE and butyrylcholinesterase (BChE) activity have not been reported. Here, we report the synthesis and testing of 36 new coumarin–chalcone hybrids (5d–7j, 9d–11f, 12k–13m) against AChE and BChE. The nature and position of the chalcone substituents had major effects on inhibitory activity as well as selectivity for AChE over BChE. Compounds with para-substituted chalcone fragments in which the substituents were choline-like had potent activity against AChE and poor activity against BChE, while ortho-substituted analogs exhibited an opposite effect. Replacement of the terminal amine groups by amide, alkyl or alkenyl groups abrogated activity. Compound 5e showed potent inhibitory activity (IC50=0.15±0.01μmol/L) and good selectivity for AChE over BChE (ratio 27.4), and a kinetic study showed that 5e exhibited mixed-type inhibition against AChE. Computational docking results indicate that 5e binds to Trp 279, Tyr334 and Trp 84 in AChE, but only to Trp 82 in BChE. Overall, the results show that coumarin–chalcone hybrids with choline-like side-chains have promising activity and selectivity against AChE and be promising therapeutic leads for Alzheimer’s disease.
- Kang, Lu,Gao, Xiao-Hui,Liu, Hao-Ran,Men, Xue,Wu, Hong-Nian,Cui, Pei-Wu,Oldfield, Eric,Yan, Jian-Ye
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p. 893 - 906
(2018/06/26)
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- RESORCINOL DERIVATIVE AS HSP90 INHIBITOR
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The present invention relates to a compound represented by formula (I) of a resorcinol derivative as an HSP90 inhibitor or pharmaceutically accepted salts thereof. The compound in the present invention has the activity of inhibiting heat shock protein HSP90. Therefore, the compound in the present invention is used to treat proliferative diseases such as cancer and neurodegenerative diseases. The present invention further provides the compounds and preparation methods for pharmaceutical compositions comprising the compounds, a method for treating diseases, and pharmaceutical compositions comprising the compounds.
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Paragraph 0129
(2017/12/27)
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- Cu(II)-Mediated keto C(sp3)-H bond α-acyloxylation of N, N-dialkylamides with aromatic carboxylic acids
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The selective oxidative coupling of aromatic carboxylic acids with the C(sp3)-H bond adjacent to the keto group of alkylamides has been developed by employing a low cost copper source. This provides an efficient approach for synthesis of O-benzoylglycolamides. The protocol displayed good functional group tolerance. A broad range of benzoic acids directly coupled with alkylamides to afford a variety of O-benzoylglycolamides in moderate to good yields. In addition, a reasonable radical mechanism was proposed based on EPR experiments.
- Li, Wenjing,Yin, Changzhen,Yang, Xiao,Liu, Hailong,Zheng, Xueli,Yuan, Maolin,Li, Ruixiang,Fu, Haiyan,Chen, Hua
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supporting information
p. 7594 - 7599
(2017/09/27)
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- The acetamide derivative
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[Problem] acetamide derivative in a high yield can be obtained, which facilitates separation of the products, and, to reduce the environmental impact of the acetamide derivative manufacturing method can be easily applied to an industrial process. (1) repr
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Paragraph 0031; 0033
(2017/06/09)
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- Design, Synthesis, and Biological Evaluation of Scutellarein Derivatives Based on Scutellarin Metabolic Mechanism in Vivo
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Three series of scutellarein derivatives have been designed and synthesized based on metabolic mechanism of scutellarin (1) in vivo. Their thrombin inhibition activities were tested through the analyzation of prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT), and fibrinogen (FIB). The antioxidant activities of these target products were assessed by 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) assay and the ability to protect PC12 cells against H2O2-induced cytotoxicity, and their solubilities were evaluated by ultraviolet (UV) spectrophotometer. The results showed that the two isopropyl groups substituted derivative (18c) demonstrated stronger anticoagulant activity, better water solubility, and good antioxidant activity compared with scutellarein (2), which warrants further development of 18c as a promising agent for ischemic cerebrovascular disease treatment. Three series of scutellarein derivatives have been designed and synthesized based on metabolic mechanism of scutellarin (1) in vivo. The results of the biological evaluation showed that the two isopropyl groups substituted derivative (18c) demonstrated stronger anticoagulant activity, better water solubility, and good antioxidant activity compared with scutellarein (2), which warrants further development of 18c as a promising agent for ischemic cerebrovascular disease treatment.
- Dong, Ze-Xi,Shi, Zhi-Hao,Li, Nian-Guang,Zhang, Wei,Gu, Ting,Zhang, Peng-Xuan,Wu, Wen-Yu,Tang, Yu-Ping,Fang, Fang,Xue, Xin,Li, He-Min,Cheng, Hai-Bo,Yang, Jian-Ping,Duan, Jin-Ao
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p. 946 - 957
(2016/05/24)
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- A 2 - (dimethylamino) - 2-oxo-ethyl-2 - (4-hydroxy phenyl) acetic acid methyl ester preparation method
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The invention discloses a preparation method of 2-(dimethylamino)-2-oxoethyl-2-(4-hydroxyphenyl) methyl acetate, which comprises the steps of allowing dimethylamine to react with chloroacetyl chloride to generate N,N-dimethyl-2-chloroacetamide, allowing N,N-dimethyl-2-chloroacetamide to react with p-hydoxyphenylactic acid to generate a crude product of 2-(dimethylamino)-2-oxoethyl-2-(4-hydroxyphenyl) methyl acetate, and refining the crude product to form a fine product of 2-(dimethylamino)-2-oxoethyl-2-(4-hydroxyphenyl) methyl acetate. 2-(dimethylamino)-2-oxoethyl-2-(4-hydroxyphenyl) methyl acetate prepared by the method is high in quality and purity, and the preparation method is simple, low in energy consumption and low in cost.
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Paragraph 0016; 0017
(2016/11/24)
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- A methanesulfonic acid the card not takes charge of he process for the preparation of intermediates
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The invention discloses a preparation method of methanesulfonic acid camostat. The method comprises the following steps: dimethylamine reacts with chloroacetyl chloride to obtain 3-pyrrolidone hydrochloride, a 3-pyrrolidone hydrochloride crude product is added with hydroxyphenylacetic acid and triethylamine to obtain methanesulfonic acid camostat, and a methanesulfonic acid camostat product is prepared from the obtained methanesulfonic acid camostat. The methanesulfonic acid camostat prepared by adopting the method is good in quality, high in yield, less in energy consumption and low in cost, and meanwhile, the preparation method is simple.
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Paragraph 0015; 0016
(2017/03/08)
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- Synthesis of scutellarein derivatives to increase biological activity and water solubility
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In order to improve the biological activity and water solubility of scutellarin (1), some derivatives of its main metabolite (scutellarein) were designed and synthesized. All the compounds were tested for their thrombin inhibition activity through the analyzation of thrombin time (TT), activated partial thromboplastin time (APTT), prothrombin time (PT) and fibrinogen (FIB). Their antioxidant activities were assessed by measuring their scavenging capacities toward 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and the ability to protect PC12 cells against H2O2-induced cytotoxicity, their water solubility were also assessed by ultraviolet (UV) spectrophotometer. The results showed that compound 8b demonstrated stronger anticoagulant and antioxidant activity, better water solubility compared with scutellarein (2), which warrants it as a promising agent for the treatment of ischemic cerebrovascular disease.
- Shi, Zhi-Hao,Li, Nian-Guang,Shi, Qian-Ping,Zhang, Wei,Dong, Ze-Xi,Tang, Yu-Ping,Zhang, Peng-Xuan,Gu, Ting,Wu, Wen-Yu,Fang, Fang,Xin-Xue,Li, He-Min,Yang, Jian-Ping,Duan, Jin-Ao
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p. 6875 - 6884
(2015/11/11)
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- SUBSTITUTED HYDANTOINS
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This invention relates to compounds of formula I: or pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, and R6 are described in this application. These compounds inhibit the enzymes MEK 1 and MEK2, protein kinases that are components o
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Page/Page column 10-11
(2009/03/07)
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- PROTEIN KINASE INHIBITOR
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The present invention provides a protein kinase inhibitor (excluding c-Jun N-terminal kinase inhibitor) which comprises, as an active ingredient, an indazole derivative represented by Formula (I) (wherein R1 represents substituted or unsubstituted aryl or a substituted or unsubstituted heterocyclic group) or a pharmaceutically acceptable salt thereof.
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Page/Page column 37
(2010/11/08)
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- Synthesis, pharmacology and?molecular modeling of?N-substituted 2-phenyl-indoles and?benzimidazoles as?potent GABAA agonists
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Among the known non-benzodiazepine hypnotic drugs, Zolpidem (1a), Indiplon (2a) and Zaleplon (2b) have shown high affinity and selectivity for the α1 subunit of the GABA-A receptor. Our group has performed pharmacophoric and ADMET-prediction studies to evaluate a virtual library of new molecules based on privileged structures. Among these, we have synthesized a library of N-substituted indoles and a library of N-substituted benzimidazoles. Afterwards, in vitro screening and in vivo spontaneous motor activity in mice has revealed molecules with good in vitro affinities for the α1 receptor and potent in vivo induction of sedation.
- Falcó, José Luis,Piqué, Maria,González, Miguel,Buira, Irma,Méndez, Eva,Terencio, Jose,Pérez, Cristina,Príncep, Marta,Palomer, Albert,Guglietta, Antonio
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p. 985 - 990
(2007/10/03)
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- Deprotonation of β,β-disubstituted α,β-unsaturated amides -Mechanism and stereochemical consequences
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A detailed study of the lithium dialkylamide induced deprotonation of β,β-disubstituted α,β-unsaturated amides is presented. The preferential γ-Z-deprotonation and stereochemical outcome of substituents on the γ-Z carbon atom are rationalized in terms of a cyclic eight-membered transition state, which is supported by DFT calculations. Analogous deprotonations on cyclohexylidenecarboxamides reveal a delicate balance of the preference for the eight-membered cyclic transition state with the effects of existing substituents on the ring and the intervention of a twist-boat transition state.
- Green, James R.,Majewski, Marek,Snieckus, Victor
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p. 1397 - 1410
(2007/10/03)
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- Cis-imidazolines
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The present invention provides compounds according to formula I having the designations provided herein, and pharmaceutically acceptable salts and esters thereof. These compounds inhibit the interaction of MDM2 protein with a p53-like peptide and have antiproliferative activity.
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- Synthesis, spectral studies and anti-inflammatory activity of glycolamide esters of niflumic acid as potential prodrugs
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In order to reduce the gastric irritation caused by direct contract mechanism of the carboxylic acid group, a series of glycolamide esters of niflumic (CAS 4394-00-7) (1) have been prepared as biolabile prodrugs by reacting appropriate 2-chloroacetamides with niflumic acid. The required 2-chloroacetamides were obtained by the condensation of chloroacetyl chloride and corresponding amine. Their structures were confirmed by UV, IR and 1H NMR spectra. Selected compounds were evaluated for anti-inflammatory activity in carrageenan induced paw oedema in rats at the doses of 45, 90 and 150 mg/kg b.w. Prodrugs showed comparable anti-inflammatory activity (67.1-79.4%) at 150 mg/kg b.w. with respect to niflumic acid (70.3%) at 45 mg/kg b.w., indicating moderate release of niflumic acid in vivo. The highest activity was observed with diethylamine (4) and pyrrolidine (9) derivatives.
- Gadad, Andanappa K.,Bhat, Shailija,Tegeli, Varsha S.,Redasani, Vivek V.
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p. 817 - 821
(2007/10/03)
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- Broadening of the substrate tolerance of α-chymotrypsin by using the carbamoylmethyl ester as an acyl donor in kinetically controlled peptide synthesis
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In the kinetically controlled approach of peptide synthesis mediated by α-chymotrypsin, the broadening of the protease's substrate tolerance is achieved by switching the acyl donor from the conventional methyl ester to the carbamoylmethyl ester. Thus, as a typical example, the extremely low coupling efficiency obtained by employing the methyl ester of an inherently poor amino acid substrate, Ala, is significantly improved by the use of this particular ester. Its ameliorating effect is observed also in the couplings of other amino acid residues such as Gly and Ser as carboxy components.
- Miyazawa, Toshifumi,Tanaka, Kayoko,Ensatsu, Eiichi,Yanagihara, Ryoji,Yamada, Takashi
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- Azulene derivatives
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The invention provides novel azulene derivatives of general formula I wherein R1 to R6 have the significance given in the description, as well as their tautomers, enantiomers, diastereomers, racemates and physiologically compatible salts or esters and substances which are hydrolyzed or metabolized in vivo to compounds of formula I. The invention is also concerned with a process and intermediates for the manufacture of the above compounds, pharmaceutical compositions which contain such compounds as well as the use of these compounds in the treatment of inflammatory conditions.
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- Synthesis of Dibenzocrown Ethers with Pendent Amide Groups
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Synthetic routes to twenty six crown ether compounds with pendent amide, N-alkylamide, or N,N-dialkylamide groups are reported.The new crown ether compounds are based on sym-dibenzo-16-crown-5-oxyacetamide and sym-(propyl)-dibenzo-16-crown-5-oxyacetamide and are obtained in high yields.
- Kasprzyk, Stanislaw P.,Bartsch, Richard A.
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p. 119 - 123
(2007/10/02)
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- REACTIONS OF P(IV)-ACID DIMETHYLAMIDES WITH ACETYL CHLORIDE
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Substitution of the dimethylamino group by chlorine in a series of P=O and P=S P(IV)-acid dimethylamides by means of acetyl chloride proceeds more readily for P=O amides.
- Nuretdinova, O. N.,Guseva, F. F.,Troitskaya, L. B.
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p. 2493 - 2495
(2007/10/02)
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- Phase-Transfer-Catalyzed Michaelis-Becker Reaction
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Dialkyl hydrogen phosphonates or dialkylphosphine oxides are conveniently and efficiently alkylated by alkyl chlorides to produce dialkyl alkylphosphonates or trialkylphosphine oxides, respectively, by aqueous sodium hydroxide in a liquid-liquid phase-transfer-catalyzed reaction.Despite the hydrolytic instability of dialkyl hydrogen phosphonates, their reaction with chloroacetamides in the two-phase system can provide dialkyl (carbamoylmethyl)phosphonates (RO)2P(O)CH2C(O)NR'R" in 90percent yields and crude purities.Many of these products have unique utility as solvent extraction reagents for the fractionation of hazardous radionuclides.The new route is not plagued by the side reactions typical of conventional Arbuzov or Michaelis-Becker syntheses, which seriously limit yields and crude product purities.It does not require anhydrous conditions or the use of alkali metals, alkoxides, or hydrides and provides access to products outside the scope of conventional routes.
- Kem, Kenneth M.,Nguyen, Nghi V.,Cross, Dennis J.
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p. 5188 - 5192
(2007/10/02)
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