- Microwave-Assisted Synthesis, Antimicrobial Activity, and SAR Study of 3-(2-Chlorobenzyl)-6-(Substituted Phenyl)-7H-[1,2,4]Triazolo[3,4-b][1,3,4]Thiadiazines
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Abstract: An efficient, simple, and greener method has been described for the synthesis of 3-(2-chlorobenzyl)-6-(substituted phenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines by using microwave irradiations. The one-pot reaction between 4-amino-5-(2-chlorobenzyl)-4H-1,2,4-triazole-3-thiol and various phenacyl bromide in the presence of reusable catalyst DABCO and EtOH solvents to give the desired products. We have discovered different organic compounds as antimicrobial agents and study for their structure-activity relationships (SAR). The antimicrobial screening shows moderate activities against used microbes.
- Joshi, Hitendra S.,Kalavadiya, Prakash L.,Tejal, D. Bhatt
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p. 1105 - 1113
(2021/10/26)
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- Palladium-Catalyzed [4 + 3] or [2 + 2 + 3] Annulation via C-H Activation and Subsequent Decarboxylation: Access to Heptagon-Embedded Polycyclic Aromatic Hydrocarbons
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The construction of a seven-membered ring in the polycyclic aromatic hydrocarbon skeleton remains a notoriously difficult but attractive challenge. Herein a novel palladium-catalyzed [4 + 3] decarboxylative annulation of 2-iodobiphenyls with 2-(2-halophenyl)acrylic acids is reported, which provides an efficient approach for assembling various tribenzo[7]annulenes via a C-H activation and decarboxylation process. Moreover, tribenzo[7]annulenes can be also synthesized via a [2 + 2 + 3] decarboxylative annulation strategy by employing readily available 1,2-halobenzenes, phenylboronic acids, and 2-(2-halophenyl)acrylic acids.
- Yang, Xiumei,Chen, Xiahong,Xu, Yankun,Zhang, Minghao,Deng, Guobo,Yang, Yuan,Liang, Yun
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supporting information
p. 2610 - 2615
(2021/04/12)
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- Cerium-Catalyzed C-H Functionalizations of Alkanes Utilizing Alcohols as Hydrogen Atom Transfer Agents
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Modern photoredox catalysis has traditionally relied upon metal-to-ligand charge-transfer (MLCT) excitation of metal polypyridyl complexes for the utilization of light energy for the activation of organic substrates. Here, we demonstrate the catalytic application of ligand-to-metal charge-transfer (LMCT) excitation of cerium alkoxide complexes for the facile activation of alkanes utilizing abundant and inexpensive cerium trichloride as the catalyst. As demonstrated by cerium-catalyzed C-H amination and the alkylation of hydrocarbons, this reaction manifold has enabled the facile use of abundant alcohols as practical and selective hydrogen atom transfer (HAT) agents via the direct access of energetically challenging alkoxy radicals. Furthermore, the LMCT excitation event has been investigated through a series of spectroscopic experiments, revealing a rapid bond homolysis process and an effective production of alkoxy radicals, collectively ruling out the LMCT/homolysis event as the rate-determining step of this C-H functionalization.
- An, Qing,Chen, Yuegang,Liu, Weimin,Pan, Hui,Wang, Xin,Wang, Ziyu,Zhang, Kaining,Zuo, Zhiwei
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supporting information
p. 6216 - 6226
(2020/04/27)
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- Divergent Photocatalytic Reactions of α-Ketoesters under Triplet Sensitization and Photoredox Conditions
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The long-lived triplet excited states of transition metal photocatalysts can activate organic substrates via either energy- or electron-transfer pathways, and the rates of these processes can be influenced by rational tuning of the reaction conditions. The characteristic reactive intermediates generated, however, are distinct and can exhibit very different reactivity patterns. This mechanistic diversity available to photocatalytic reactions might thus offer an opportunity to engineer divergent reactions that give markedly different chemical outcomes under superficially similar conditions. Herein, we show that the photocatalytic reactions of benzoylformate esters with alkenes can be directed toward either Paternò-Büchi cycloadditions or allylic functionalization reactions under conditions favoring energy transfer or electron transfer, respectively. These studies provide a framework for designing other divergent photocatalytic methods that produce different sets of reaction outcomes under photoredox and triplet sensitization conditions.
- Dong, Xiao,Yoon, Tehshik P.,Zheng, Jian
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supporting information
(2020/09/02)
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- Blue Light-Promoted N?H Insertion of Carbazoles, Pyrazoles and 1,2,3-Triazoles into Aryldiazoacetates
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Blue light irradiation of aryldiazoacetates leads to the formation of free carbenes, which can react with carbazoles, pyrazoles and 1,2,3-triazoles to afford the corresponding N?H inserted products. These reactions are performed under air and at room temperature, allowing the mild preparation of a variety of motifs found in biologically relevant targets. (Figure presented.).
- Stivanin, Mateus L.,Fernandes, Alessandra A. G.,da Silva, Amanda F.,Okada, Celso Y.,Jurberg, Igor D.
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supporting information
p. 1106 - 1111
(2020/01/25)
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- Synthesis and bio-evaluation of natural butenolides-acrylate conjugates
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A series of novel 3-aryl-4-hydroxy-2(5H) furanone-acrylate hybrids were designed and synthesized based on the natural butenolides and acrylates scaffolds. The structures of the prepared compounds were characterized by 1H-NMR, 13C-NMR and electrospray ionization mass spectrometry (ESI-MS), and the bioactivity of the target compounds against twelve phytopathogenic fungi was investigated. The preliminary in vitro antifungal activity screening showed that most of the target compounds had moderate inhibition on various pathogenic fungi at the concentration of 100 mg·L?1, and presented broad-spectrum antifungal activities. Further studies also indicated that compounds 7e and 7k still showed some inhibitory activity against Pestallozzia theae, Sclerotinia sclerotiorum and Gibberella zeae on rape plants at lower concentrations, which could be optimized as a secondary lead for further research.
- Bao, Longzhu,Wang, Shuangshuang,Song, Di,Wang, Jingjing,Cao, Xiufang,Ke, Shaoyong
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- Dehydroxymethylation of alcohols enabled by cerium photocatalysis
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Dehydroxymethylation, the direct conversion of alcohol feedstocks as alkyl synthons containing one less carbon atom, is an unconventional and underexplored strategy to exploit the ubiquity and robustness of alcohol materials. Under mild and redox-neutral reaction conditions, utilizing inexpensive cerium catalyst, the photocatalytic dehydroxymethylation platform has been furnished. Enabled by ligand-to-metal charge transfer catalysis, an alcohol functionality has been reliably transferred into nucleophilic radicals with the loss of one molecule of formaldehyde. Intriguingly, we found that the dehydroxymethylation process can be significantly promoted by the cerium catalyst, and the stabilization effect of the fragmented radicals also plays a significant role. This operationally simple protocol has enabled the direct utilization of primary alcohols as unconventional alkyl nucleophiles for radical-mediated 1,4-conjugate additions with Michael acceptors. A broad range of alcohols, from simple ethanol to complex nucleosides and steroids, have been successfully applied to this fragment coupling transformation. Furthermore, the modularity of this catalytic system has been demonstrated in diversified radical-mediated transformations including hydrogenation, amination, alkenylation, and oxidation.
- Zhang, Kaining,Chang, Liang,An, Qing,Wang, Xin,Zuo, Zhiwei
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supporting information
p. 10556 - 10564
(2019/08/20)
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- Dehydroxymethylation of Alcohols Enabled by Cerium Photocatalysis
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Dehydroxymethylation, the direct conversion of alcohol feedstocks as alkyl synthons containing one less carbon atom, is an unconventional and underexplored strategy to exploit the ubiquity and robustness of alcohol materials. Under mild and redox-neutral reaction conditions, utilizing inexpensive cerium catalyst, the photocatalytic dehydroxymethylation platform has been furnished. Enabled by ligand-to-metal charge transfer catalysis, an alcohol functionality has been reliably transferred into nucleophilic radicals with the loss of one molecule of formaldehyde. Intriguingly, we found that the dehydroxymethylation process can be significantly promoted by the cerium catalyst, and the stabilization effect of the fragmented radicals also plays a significant role. This operationally simple protocol has enabled the direct utilization of primary alcohols as unconventional alkyl nucleophiles for radical-mediated 1,4-conjugate additions with Michael acceptors. A broad range of alcohols, from simple ethanol to complex nucleosides and steroids, have been successfully applied to this fragment coupling transformation. Furthermore, the modularity of this catalytic system has been demonstrated in diversified radical-mediated transformations including hydrogenation, amination, alkenylation, and oxidation.
- Zhang, Kaining,Chang, Liang,An, Qing,Wang, Xin,Zuo, Zhiwei
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supporting information
p. 10556 - 10564
(2019/08/28)
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- Stereoselective synthesis of 3,4-di-substituted mercaptolactones via photoredox-catalyzed radical addition of thiophenols
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A visible light mediated radical addition of thiophenols on 4-phenylbut-3-enoic acids to give diastereoselective synthesis of 3,4-disubstituted γ-lactones is reported. The reaction precludes the conventional prerequisite of conjugate addition. Furthermore, the lactones were successfully utilized in the synthesis of γ-ketoamides.
- Kouser, Farzana,Sharma, Vijay Kumar,Rizvi, Masood,Sultan, Shaista,Chalotra, Neha,Gupta, Vivek K.,Nandi, Utpal,Shah, Bhahwal Ali
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supporting information
p. 2161 - 2166
(2018/05/05)
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- Comparison of Phenylacetates with Benzoates and Phenylpropanoates as Antifeedants for the Pine Weevil, Hylobius abietis
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This study concludes an extensive investigation of antifeedants for the pine weevil, Hylobius abietis (Coleoptera: Curculionidae), an economically important pest of planted conifer seedlings. Building on the previously reported antifeedant effects of benzoates and phenylpropanoids (aromatic compounds with one- or three-carbon-atom substituents on the benzene ring), we here report the antifeedant effects of compounds with two-carbon-atom side chains (i.e., phenylacetates). We also present new results; the best antifeedants from the benzoate class were tested at 10-fold lower concentrations in order to find the optimal antifeedants. Generally, for all three compound classes, efficient antifeedants were found to have one or two methyl, chloro, or methoxy substituents on the aromatic ring. For monosubstituted phenylpropanoids, the substituent preferably should be in the para-position. In the search for synergistic antifeedant effects among the three compound classes, combinations of compounds from the three classes were tested in binary and ternary mixtures.
- Unelius, C. Rikard,Bohman, Bj?rn,Nordlander, G?ran
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p. 11797 - 11805
(2018/11/21)
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- Palladium-Catalyzed Carbonylative Direct Transformation of Benzyl Amines under Additive-Free Conditions
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In this communication, we developed a new procedure for the direct carbonylative transformation of benzyl amines. Using dimethyl carbonate as the solvent, methyl 2-arylacetates can be produced in good to excellent yields from the corresponding primary, secondary, and tertiary benzyl amines with palladium as the catalyst. Notably, no base or any other additive is required here. In addition, our procedure can also be applied in the preparation of methylphenidate, which is a marketing drug and used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy.
- Li, Yahui,Wang, Zechao,Wu, Xiao-Feng
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p. 738 - 741
(2018/01/17)
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- The computer-aided discovery of novel family of the 5-HT6 serotonin receptor ligands among derivatives of 4-benzyl-1,3,5-triazine
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The work describes a discovery of new chemical family of potent ligands for the 5-HT6 serotonin receptors. During the search for new histamine H4 receptor antagonists among 1,3,5-triazine derivatives, compound 2 (4-benzyl-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine) was found. Compound 2, weakly active for the H4 receptor but fitted in 3/4 of pharmacophore features of the 5-HT6R ligand, occurred to be a moderate 5-HT6R agent, useful as a lead structure for further modifications. A series of new derivatives (3–19) of the lead 2 was synthesized, evaluated in the radioligand binding assay (RBA) and explored in comprehensive molecular modelling, including both pharmacophore- and structure-based approaches with docking to the homology model of 5-HT6R. The most active compounds displayed a potent affinity for the 5-HT6R in the nanomolar range (Ki?=?20–30?nM), some of them (4, 11 and 19) were tested in the rat forced swim test that revealed their antidepressant-like effect. SAR-analysis on the basis of both, RBA and docking results, indicated that action on the receptor is related to the hydrophobicity and the size of aromatic moiety substituted by a methylene linker at the position 4 of 1,3,5-triazine.
- ?a?ewska, Dorota,Kurczab, Rafa?,Wi?cek, Ma?gorzata,Kamińska, Katarzyna,Sata?a, Grzegorz,Jastrz?bska-Wi?sek, Magdalena,Partyka, Anna,Bojarski, Andrzej J.,Weso?owska, Anna,Kie?-Kononowicz, Katarzyna,Handzlik, Jadwiga
-
supporting information
p. 117 - 124
(2017/04/26)
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- Discovery, synthesis, and structure-activity relations of 3,4-dihydro-1H-spiro(naphthalene-2,2′-piperidin)-1-ones as potassium-competitive acid blockers
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With the aim to discover a gastric antisecretory agent more potent than the existing proton pump inhibitors, novel 3,4-dihydro-1H-spiro(naphthalene-2,2′-piperidin)-1-one derivatives, which could occupy two important lipophilic pockets (described as LP-1 and LP-2) of H+,K+-ATPase and can strongly bind to the K+-binding site, were designed based on a docking model. Among the compounds synthesized, compound 4d showed a strong H+,K+-ATPase-inhibitory activity and a high stomach concentration in rats, resulting in potent inhibitory action on histamine-stimulated gastric acid secretion in rats. Furthermore, 4d exerted significant inhibitory action on histamine-stimulated gastric-acid secretion in rats with a rapid onset and moderate duration of action after the administration. These findings may lead to a new insight into the drug design of potassium-competitive acid blockers.
- Imaeda, Toshihiro,Ono, Koji,Nakai, Kazuo,Hori, Yasunobu,Matsukawa, Jun,Takagi, Terufumi,Fujioka, Yasushi,Tarui, Naoki,Kondo, Mitsuyo,Imanishi, Akio,Inatomi, Nobuhiro,Kajino, Masahiro,Itoh, Fumio,Nishida, Haruyuki
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p. 3719 - 3735
(2017/06/13)
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- An approach to spirooxindoles: Via palladium-catalyzed remote C-H activation and dual alkylation with CH2Br2
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A facile and efficient approach for the synthesis of spirooxindoles has been developed via the coupling of spirocyclic C,C-palladacycles with CH2Br2. The key spirocyclic palladacycles are generated catalytically via remote C-H activation. A range of spirooxindoles can be synthesized in good to excellent yields from readily available starting material.
- Shao, Changdong,Wu, Zhuo,Ji, Xiaoming,Zhou, Bo,Zhang, Yanghui
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supporting information
p. 10429 - 10432
(2017/09/25)
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- Synthesis and Biological Evaluation of New (-)-Gossypol-Derived Schiff Bases and Hydrazones
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A series of 14 new (-)-gossypol Schiff bases and hydrazones have been synthesized via an in situ procedure in high yields. Structural data showed that all target compounds exist as the enamine tautomer. Bioassays showed that several compounds exhibited cytotoxic effects against three human cancer cell lines. Compound 8a showed the greatest cytotoxic effect against hepatocellular carcinoma (HepG2), lung carcinoma (LU-1), and breast cancer (MCF-7) cell lines with IC50 values of 20.93, 13.58, and 9.40 μM, respectively. However, in an antibacterial test, compounds 8a and 8b inhibited Staphylococcus aureus and Bacillus cereus and compound 8e inhibited only Staphylococcus aureus at the same MIC values of 1024 μg/ml.
- Vu, Vu Van,Nhung, Trinh Thi,Thanh, Nguyen Thi,Chinh, Luu Van,Tien, Vu Dinh,Thuy, Vu Thu,Thi Thao, Do,Nam, Nguyen Hai,Koeckritz, Angela,Vu, Tran Khac
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-
- ANTI-HCMV COMPOSITIONS AND METHODS
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This document relates to compounds useful as agents for preventing or treating human cytomegalovirus (HCMV) infections.
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Page/Page column 31; 32; 49
(2016/06/06)
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- Copper-Catalyzed Regiospecific and 1,2-Regioselective Cyclopropanation of (1 Z)-1-Amino- and (1 Z)-1-Oxy-1,3-butadienyl Derivatives
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The copper-catalyzed regiospecific and 1,2-regioselective cyclopropanation of (1Z)-1-amino- and (1Z)-1-oxy-1,3-butadienyl derivatives, which could be prepared by Z-stereoselective 1,4-elimination with α-aryl diazoesters was successfully demonstrated. This successful regiospecific protocol enabled the preparation of the corresponding 1-amino- and 1-oxy-2-vinylcyclopropane derivatives as almost single stereoisomers.
- Tayama, Eiji,Saito, Shun
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supporting information
p. 1880 - 1884
(2015/08/06)
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- Synthesis of Quinolines by Visible-Light Induced Radical Reaction of Vinyl Azides and α-Carbonyl Benzyl Bromides
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A visible-light induced radical reaction of vinyl azides and α-carbonyl benzyl bromides was developed, which provides an efficient route to polysubstituted quinolines via a C-C and C-N bond formation sequence.
- Wang, Qile,Huang, Jun,Zhou, Lei
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supporting information
p. 2479 - 2484
(2015/08/18)
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- Synthesis and biological evaluation of novel 3,4-diaryl lactam derivatives as triple reuptake inhibitors This article is dedicated to Professor Jahyo Kang for his lifelong commitment to mentoring graduate students
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A series of 3,4-diarylpyrrolidin-2-one was designed, prepared and evaluated as triple reuptake inhibitors for antidepressant. Most compounds exhibited comparable in vitro efficacy as norepinephrine and dopamine transporter reuptake inhibitors. Especially, 2i showed better potency than GBR-12909 (IC 50 = 14 nM) which was used as reference compound for dopamine transporter. In addition, 2a and 2b showed inhibition (5.17 μM-85.6 nM) for three transporters.
- Park, Jung-Eun,Song, Chiman,Choi, Keehyun,Sim, Taebo,Moon, Bongjin,Roh, Eun Joo
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supporting information
p. 5515 - 5518
(2013/10/01)
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- Regio- and chemoselective C-H chlorination/bromination of electron-deficient arenes by weak coordination and study of relative directing-group abilities
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It's all relative: A practical and efficient PdII-catalyzed regio- and chemoselective chlorination/bromination has been developed for the facile synthesis of a broad range of aromatic chlorides. The reaction demonstrates excellent reactivity, good functional-group tolerance, and high yields. A preliminary study was conducted to evaluate relative directing-group abilities of various functionalities. Copyright
- Sun, Xiuyun,Shan, Gang,Sun, Yonghui,Rao, Yu
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supporting information
p. 4440 - 4444
(2013/05/22)
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- PROCESS FOR THE PREPARATION OF (3ARS,12BRS)-5-CHLORO-2-METHYL-2,3,3A12B-TETRAHYDRO-1HDIBENZO[2,3:6,7] OXEPINO [4,5-C]PYRROLE MALEATE AND IT'S PHARMACEUTICAL COMPOSITION THEREOF
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The present invention relates to an improved process for the preparation (3aRS,12bRS)-5-Chloro-2-menthyl-2,3,3a,12b-tetrahydro-1Hdibenzo[2,3:6,7]oxepino [4,5-c]pyrrole maleate represented by the compound of formula-1a and its pharmaceutical composition.(F)
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Page/Page column 34
(2012/04/10)
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- CYCLOPROPYL DERIVATIVES AND METHODS OF USE
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The disclosure relates to cyclopropyl derivatives and methods of use. In some embodiments, the disclosure relates to methods of managing medical disorders with pharmaceutical compositions disclosed herein administered to subject in need thereof. In certain embodiments, the disclosure relates to methods of managing mental disorders, mood disorders, pain, and fibromyalgia and related conditions with pharmaceutical compositions disclosed herein.
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Page/Page column 31
(2012/11/07)
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- Oxidative rearrangement of alkyl aryl/heteroaryl ketones by 1,2-aryl/heteroaryl shift using iodic acid
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A method for synthesis of α-aryl/heteroaryl alkanoic acids involving oxidative rearrangement of alkyl aryl/heteroaryl ketones by 1,2-aryl/heteroaryl shift using iodic acid is described. ARKAT-USA, Inc.
- Huddar, Sameerana N.,Deshmukh, Swapnil S.,Akamanchi, Krishnacharya G.
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experimental part
p. 67 - 75
(2011/06/19)
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- Oxidative rearrangements of arylalkanones with 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide, a 'green' analog of Koser's reagent
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Previous methods for the conversion of arylalkanones to alkyl 2-arylesters by oxidative rearrangement utilized reagents which either produced toxic metal salts or halogenated organics as by-products. In this report, 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide (HMBI) is used to effect this useful transformation, where the reduced iodine reagent is water-soluble and readily recycled.
- Justik, Michael W.
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p. 3003 - 3007
(2008/02/06)
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- PYRIMIDINE-2, 4-DIONE DERIVATIVES AS GONADOTROPIN-RELEASING HORMONE RECEPTOR ANTAGONISTS
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GnRH receptor antagonists are disclosed that have utility in the treatment of a variety of sex-hormone related conditions in both men and women. The compounds of this invention have the structure: wherein R1a, R1b, R1c, R2a, R2b, R3, R4, R5, R6 and X are as defined herein, including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof. Also disclosed are compositions containing a compound of this invention in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for antagonizing gonadotropin-releasing hormone in a subject in need thereof.
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- GONADOTROPIN-RELEASING HORMONE RECEPTOR ANTAGONISTS AND METHODS RELATING THERETO
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GnRH receptor antagonists are disclosed that have utility in the treatment of a variety of sex-hormone related conditions in both men and women. The compounds of this invention have the structure: wherein n, R1a, R1b, R1c, R2a, R2b, R3, R4, R5, R6 and X are as defined herein, including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof. Also disclosed are compositions containing a compound of this invention in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for antagonizing gonadotropin-releasing hormone in a subject in need thereof.
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- Pyrimidine derivatives useful as inhibitors of PKC-theta
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Disclosed are novel compounds of formula (I): wherein R1, R2 and R3 are as defined herein, which are useful as inhibitors of PKC-theta and are thus useful for treating a variety of diseases and disorders that are mediated or sustained through the activity of PKC-theta, including immunological disorders and type II diabetes. This invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.
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- 2,4-DIAMINOPYRIMIDINE DERIVATIVES USEFUL AS INHIBITORS OF PKC-THETA
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Disclosed are novel compounds of formula (I) wherein R1, R2 and R3 are as defined herein, which are useful as inhibitors of PKC-theta and are thus useful for treating a variety of diseases and disorders that are mediated or sustained through the activity of PKC-theta, including immunological disorders and type II diabetes. This invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders and processes for preparing these compounds.
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Page 85 - 86
(2008/06/13)
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- Synthesis and structure-antifungal activity relationships of 3-aryl-5-alkyl-2,5-dihydrofuran-2-ones and their carbanalogues: Further refinement of tentative pharmacophore group
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Two series of 3-(substituted phenyl)-5-alkyl-2,5-dihydrofuran-2-ones related to a natural product, (-)incrustoporine, were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring exhibited selective antifungal activity against the filamentous strains of Absidia corymbifera and Aspergillus fumigatus. On the other hand, the influence of the lenghth of the alkyl chain at C(5) was marginal. The antifungal effect of the most active compound against the above strains was higher than that of ketoconazole, and close to that of amphotericin B. In order to verify the hypothesis about a possible relationship between the Michael-accepting ability of the compounds and their antifungal activity, a series of simple carbanalogues, 2-(substituted phenyl)cyclopent-2-enones, was prepared and subjected to antifungal activity assay as well.
- Pour, Milan,Spulak, Marcel,Balsanek, Vojtech,Kunes, Jiri,Kubanova, Petra,Buchta, Vladimir
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p. 2843 - 2866
(2007/10/03)
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- New and efficient method for esterification of carboxylic acids with simple primary and secondary alcohols using cerium(IV) ammonium nitrate (CAN)
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The esterification of phenylacetic acids and cis-oleic acid with primary and secondary simple alcohols, which also act as solvents using cerium(IV) ammonium nitrate (CAN) at room temperature gave phenylacetates and methyl (9Z)-octadec-9-enoate. The reactions, which occur under relatively mild conditions, afforded the desired products in good to excellent yields.
- Pan, Wen-Bin,Chang, Fang-Rong,Wei, Li-Mei,Wu, Ming-Jung,Wu, Yang-Chang
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p. 331 - 334
(2007/10/03)
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- 1,2-disubstituted-6-oxo-3-phenyl-piperidine-3-carboxamides and combinatorial libraries thereof
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The invention relates to combinatorial libraries containing two or more novel piperidine-3-carboxamide derivative compounds, methods of preparing the piperidine-3-carboxamide derivative compounds and piperidine-3-carboxamide derivative compounds bound to a resin
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- SUBSTITUTED PHENYL COMPOUNDS WITH A SUBSTITUENT HAVING A 1,3-BENZODIOXOLE RING
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This invention is directed to compounds of formula I STR1 wherein R 1 is CN, CH 2 CN, CH=CHCN, CHO, or CH=CHCO. sub. 2 H;R 2 is aryl lower alkoxy, heteroaryl lower alkoxy, aryl lower alkylthio or heteroaryl lower alkylthio wherein each of the aryl and heteroaryl moieties is optionally substituted;R 3 is halogen;R 4 is optionally substituted aryl or optionally substituted heteroaryl;R. sup.5 is carboxy or an acid isostere; X is oxygen or sulphur; and n is zero or 1; or an N-oxide thereof, prodrug thereof solvate thereof, or pharmaceutically acceptable salt thereof, which compounds have endothelin antagonist activity. The invention is also directed to methods for preparing the compounds of formula I and their pharmaceutical use.
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- Substituted phenyl compounds with a substituent having a thienyl ring
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This invention is directed to compounds of formula I wherein R1 is CN, CH2CN, CH=CHCN, CHO, or CH=CHCO2H; R2 is aryl lower alkoxy, heteroaryl lower alkoxy, aryl lower alkylthio or heteroaryl lower alkylthio wherein each of the aryl and heteroaryl moieties is optionally substituted; R3 is halogen; R4 is optionally substituted aryl or optionally substituted heteroaryl; R5 is carboxy or an acid isostere; X is oxygen or sulphur; and n is zero or 1; or an N-oxide thereof, prodrug thereof solvate thereof, or pharmaceutically acceptable salt thereof, which compounds have endothelin antagonist activity. The invention is also directed to methods for preparing the compounds of formula I and their pharmaceutical use.
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- One-Step Synthesis of Methyl Esters from Nitriles
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Polyphosphate ester that contains methanol easily converts aromatic and alkyl nitriles in one step and in high yield to the corresponding methyl ester at 120 - 150 deg C.
- Mills, Frank D.,Brown, Richard T.
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p. 3131 - 3135
(2007/10/02)
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- Synthesis of phenylacetic acid esters
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Esters of phenylacetic acids are prepared in a single step by hydrolysis of 2,2,2-trichloro-1-phenylethanes in inorganic basic media.
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- Conversion of Aromatic Ketones into α-Arylalkanoic Acids. Oxidation by Thallium(III) and by Halogens
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The mechanism by which thallium (III) nitrate oxidises aromatic ketones to α-arylalkanoic acids has been investigated and the role of additives in the system elucidated.It is found that in the absence of additives an organothallium intermediate, most probably the phenacylthallium species BzCH2Tl(NO3)2, persists and that the key to an efficient rearrangement is the ready conversion of this compound into its acetal.Thallium(III) is shown not to be a unique reagent for the oxidation.Other oxidants capable of acting initially as an electrophile and then as a leaving group are equally effective, provided that formation of an acetal is possible.Iodine-silver nitrate in particular offers considerable advantages as reagent over thallium(III).Higher specificity is achieved, unwanted side-reactions can be avoided, and toxicity problems are eliminated.Bromine may be used instead of iodine, but chlorine proves unsatisfactory as an oxidant.
- Higgins, Stanley D.,Thomas, Barry C.
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p. 235 - 242
(2007/10/02)
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