- The Pd-catalyzed synthesis of difluoroethyl and difluorovinyl compounds with a chlorodifluoroethyl iodonium salt (CDFI)
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Herein, we report a simple and efficient method for the direct installation of chlorodifluoroethyl group onto aromatic molecules of various aromatic amides with a new 2-chloro,2,2-difluoroethyl(mesityl)iodonium salt (CDFI). Moreover, the chlorodifluoroeth
- Cao, Chengyao Kimmy,Chen, Chao,Ge, Chenxin,Niu, Yaru,Qu, Hongmei
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supporting information
(2021/10/01)
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- Atom-Economical and Tandem Conversion of Nitriles to N-Methylated Amides Using Methanol and Water
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A cobalt complex catalyzed tandem conversion of nitrile to N-methylated amide is described using a methanol and water mixture. Using this protocol, several nitriles were directly and efficiently converted to the desired N-methylated amides. Kinetic experiments using H2O18 and CD3OD suggested that water and methanol were the source of the oxygen atom and methyl group, respectively, in the final N-methylated amides. Importantly, the participation of active Co(I)-H species in this transformation was realized from the control experiment. The kinetic isotope effect (KIE) study suggested that the activation of the C-H bond of methanol was a kinetically important step. The Hammett plot confirmed that the reaction was faster with the electron deficient nitriles. In addition, the plausible pathway for the formation of N-methylated amides from the nitriles was supported by the computational study.
- Paul, Bhaskar,Maji, Milan,Kundu, Sabuj
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p. 10469 - 10476
(2019/11/05)
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- Ruthenium-Catalyzed Synthesis of N-Methylated Amides using Methanol
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An efficient synthesis of N-methylated amides using methanol in the presence of a ruthenium(II) catalyst is realized. Notably, applying this process, tandem C-methylation and N-methylation were achieved to synthesize α-methyl N-methylated amides. In addition, several kinetic studies and control experiments with the plausible intermediates were performed to understand this novel protocol. Furthermore, detailed computational studies were carried out to understand the mechanism of this transformation.
- Paul, Bhaskar,Panja, Dibyajyoti,Kundu, Sabuj
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supporting information
p. 5843 - 5847
(2019/08/26)
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- Base-promoted nucleophilic fluoroarenes substitution of C–F bonds
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With the use of KOH/DMSO as the superbase medium, the nucleophilic fluoroarene substitution for C–F bonds is presented. The transformation proceeds smoothly with the use of fluoroarenes bearing not only electron-withdrawing group, but also electron-donating group and a variety of nucleophiles such as alcohols, phenols, amines, amides and nitrogen-heterocyclic compounds. The double nucleophilic substitution using ortho-difluoroarenes and nucleophiles bearing ortho-dinucleophilic groups results in the formation of 2,3-dihydro-1,4-benzodioxins, dibenzo[b,e][1,4]dioxins and 10H-phenoxazines in moderate to good yields.
- Su, Ji,Chen, Qian,Lu, Le,Ma, Yuan,Auyoung, George Hong Lok,Hua, Ruimao
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supporting information
p. 303 - 307
(2017/12/11)
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- Intramolecular hydrogen bonding in medicinal chemistry
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The formation of intramolecular hydrogen bonds has a very pronounced effect on molecular structure and properties. We study both aspects in detail with the aim of enabling a more rational use of this class of interactions in medicinal chemistry. On the basis of exhaustive searches in crystal structure databases, we derive propensities for intramolecular hydrogen bond formation of five- to eight-membered ring systems of relevance in drug discovery. A number of motifs, several of which are clearly underutilized in drug discovery, are analyzed in more detail by comparing small molecule and protein-ligand X-ray structures. To investigate effects on physicochemical properties, sets of closely related structures with and without the ability to form intramolecular hydrogen bonds were designed, synthesized, and characterized with respect to membrane permeability, water solubility, and lipophilicity. We find that changes in these properties depend on a subtle balance between the strength of the hydrogen bond interaction, geometry of the newly formed ring system, and the relative energies of the open and closed conformations in polar and unpolar environments. A number of general guidelines for medicinal chemists emerge from this study
- Kuhn, Bernd,Mohr, Peter,Stahl, Martin
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experimental part
p. 2601 - 2611
(2010/08/05)
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- The scope and limitation of nickel-catalyzed aminocarbonylation of aryl bromides from formamide derivatives
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(Chemical Equation Presented) Nickel-catalyzed aminocarbonylation of aryl halides is described. A well-defined air-stable nickel-phosphite catalytic system (Ni(OAc)2 · 4H2O/phosphite 1) effectively promoted the aminocarbonylation of
- Jo, Youngshin,Ju, Jinhun,Choe, Jaehoon,Kwang, Ho Song,Lee, Sunwoo
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supporting information; experimental part
p. 6358 - 6361
(2009/12/08)
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- Efficient tandem process for the catalytic deprotection of N-allyl amides and lactams in aqueous media: A novel application of the bis(allyl)- ruthenium(IV) catalysts [Ru(η3:η2: η3-C12H18)Cl2] and [Ru(η3:η3-C10H16)-(μ-Cl) Cl}2]
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An operationally simple and highly efficient methodology for the removal of the allyl protecting group in amides and lactams has been developed by using the commercially available bis(allyl)-ruthenium(IV) catalysts [Ru(η3:η2:η3-C12H 18)Cl2] (C12H18 = dodeca-2,6,10-triene-1,12-diyl) and [(Ru(η3:η3- C10H16)(μ-Cl)Cl}2] (C10H 16 = 2,7-dimethylocta-2,6-diene-1,8-diyl). The tandem process, which takes place in aqueous media and proceeds in a one-pot manner, involves the initial isomerization of the C=C bond of the allyl unit and subsequent oxidative cleavage of the resulting enamide.
- Cadierno, Victorio,Gimeno, Jose,Nebra, Noel
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p. 6590 - 6594
(2008/03/13)
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- 11-BETA-HYDROXYSTEROID DEHYDROGENASE 1 INHIBITORS USEFUL FOR THE TREATMENT OF DIABETES, OBESITY AND DYSLIPIDEMIA
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Compounds having Formula (I), including pharmaceutically acceptable salts, hydrates and solvates thereof, are selective inhibitors of the 11β-HSD1 enzyme. The compounds are useful for the treatment of diabetes, such as noninsulin-dependent diabetes (NIDDM), hyperglycemia, obesity, insulin resistance, dylsipidemia, hyperlipidemia, hypertension, Syndrome X, and other symptoms associated with NIDDM.
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- SUBSTITUTED PIPERAZINE DERIVATIVES
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The present invention relates to substituted piperazine derivatives (herein referred to as compounds or compounds of formula (1)) or stereoisomers, or pharmaceutically acceptable salts thereof and their use as tachykinin receptor antagonists. Such antagon
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- Substituted alkyldiamine derivatives
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The present invention relates to novel substituted alkyldiamine derivatives and pharmaceutically acceptable salts thereof which are useful tachykinin antagonists. Such antagonists are useful in the treatment of tachykinin-mediated diseases and conditions including asthma, cough, and bronchitis.
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- Cyclic amide derivatives for treating asthma
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Compounds of formula I STR1 wherein Q1, Q2, Q3, and Q4 have any of the meanings given in the specification, their N-oxides, and their pharmaceutically acceptable salts are nonpeptide antagonists of neurokinin A and useful for the treatment of asthma, etc. Also disclosed are pharmaceutical compositions, processes for preparing the compounds of formula I and intermediates.
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- Photosensitized Electron-Transfer Reaction of 3-Aryl-2-methyloxaziridine: Direct Deoxygenation from the Isomeric Arylnitrone
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Photosensitized electron-transfer reactions of 3-aryl-2-methyloxaziridines gave mainly the corresponding benzaldehydes, whereas the isomeric nitrones gave imines as well as aldehydes.Deoxygenation of the nitrone occurred via the nitrone cation radical under the reaction conditions.An aryl substituent effect on the reaction and isomerizations of both cation radicals are also discussed.
- Iwano, Yasunori,Kawamura, Yasuhiko,Miyoshi, Hiroki,Yoshinari, Toshifumi,Horie, Tokunaru
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p. 2348 - 2350
(2007/10/02)
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