- Two new benzamides: Synthesis, spectroscopic characterization, X-ray diffraction, and electronic structure analyses
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This work includes the syntheses, molecular and electronic structure analyses of two novel secondary amide compounds 3-acetoxy-2-methyl-N-(2-methoxyphenyl)benzamide, 1 and 3-acetoxy-2-methyl-N-(3-methylphenyl)benzamide, 2. The title compounds were charact
- K?rca, Ba?ak Ko?ar,?akmak, ?ükriye,Yakan, Hasan,Odaba?o?lu, Mustafa,Büyükgüng?r, Orhan,Kütük, Halil
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- Synthesis and characterization of 3-acetoxy-2-methyl-N-(phenyl)benzamide and 3-acetoxy-2-methyl-N-(4- methylphenyl)benzamide
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This study treats about two successfully synthesized secondary amide compounds 3-Acetoxy-2-methyl-N-(phenyl)benzamide, I and 3-Acetoxy-2-methyl-N-(4-methylphenyl)benzamide, II. Compounds were characterized by FTIR, 1H NMR, 13C NMR and X-ray single crystal diffraction analysis techniques. Single crystal X-ray diffraction analyses show that while I crystallized in the orthorhombic system with space group Pbca, II crystallized in the triclinic system with space group P-1 and the asymmetric unit of II consists of two crystallographically independent molecules. Lattice constants are a = 7.9713 (3) ?, b = 9.5059 (3) ?, c = 37.1762 (2) ?, Z = 8 for I and a = 7.5579 (8) ?, b = 8.8601 (8) ?, c = 23.363 (3) ?, α = 97.011 (9) °, β = 96.932 (9)°, γ = 90.051 (8)°, Z = 4 for II. Crystallographic studies also show that the supramolecular structures were stabilized by intramolecular, intermolecular hydrogen bonds and C[sbnd]H … π interactions for both compounds. Characteristic amide bonds were observed in IR and NMR spectra.
- K?rca, Ba?ak Ko?ar,?akmak, ?ükriye,Kütük, Halil,Odaba?o?lu, Mustafa,Büyükgüng?r, Orhan
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- Synthesis, characterization, antioxidant, and antibacterial activities of new 2,3-dimethoxy and 3-acetoxy-2-methyl benzamides
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Abstract: We performed a series of novel benzamide compounds which were synthesized starting from 2,3-dimethoxybenzoic acid or 3-acetoxy-2-methylbenzoic acid and amine derivatives. All the obtained products were purified, and the analysis of these product
- Yakan, Hasan,Cakmak, Sukriye,Kutuk, Halil,Yenigun, Semiha,Ozen, Tevfik
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- Rhodium-Catalyzed Alkylation of C?H Bonds in Aromatic Amides with Non-activated 1-Alkenes: The Possible Generation of Carbene Intermediates from Alkenes
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The alkylation of C?H bonds (hydroarylation) in aromatic amides with non-activated 1-alkenes using a rhodium catalyst and assisted by an 8-aminoquinoline directing group is reported. The addition of a carboxylic acid is crucial for the success of this reaction. The results of deuterium-labeling experiments indicate that one of deuterium atoms in the alkene is missing, suggesting that the reaction does not proceed through the commonly accepted mechanism for C?H alkylation reactions. Instead the reaction is proposed to proceed through a carbene mechanism. The carbene mechanism is also supported by preliminary DFT calculations.
- Yamaguchi, Takuma,Natsui, Satoko,Shibata, Kaname,Yamazaki, Ken,Rej, Supriya,Ano, Yusuke,Chatani, Naoto
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supporting information
p. 6915 - 6919
(2019/05/10)
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- Rhodium-Catalyzed Alkenylation of C-H Bonds in Aromatic Amides with Alkynes
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The rhodium-catalyzed alkenylation of C-H bonds of aromatic amides with alkynes is reported. A variety of functional groups, including OMe, OAc, Br, Cl, and even NO2, are applicable to this reaction to give the corresponding hydroarylation prod
- Shibata, Kaname,Natsui, Satoko,Chatani, Naoto
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supporting information
p. 2234 - 2237
(2017/05/12)
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- BORON-CONTAINING DIACYLHYDRAZINES
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The present disclosure provides boron-containing diacylhydrazines having Formula I: and the pharmaceutically acceptable salts and solvates thereof, wherein R1, R2, R3, R4, and R5 are defined as set forth in the specification. The present disclosure also provides the use of boron-containing diacylhydrazines is ecdysone receptor-based inducible gene expression systems. Thus, the present disclosure is useful for applications such as gene therapy, treatment of disease, large scale production of proteins and antibodies, cell-based screening assays, functional genomics, proteomics, metabolomics, and regulation of traits in transgenic organisms, where control of gene expression levels is desirable.
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Paragraph 0522
(2014/09/29)
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- Ni(II)-catalyzed oxidative coupling between C(sp2)-H in benzamides and C(sp3)-H in toluene derivatives
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Oxidative coupling between C(sp2)-H bonds and C(sp3)-H bonds is achieved by the Ni(II)-catalyzed reaction of benzamides containing an 8-aminoquinoline moiety as the directing group with toluene derivatives in the presence of heptafluoroisopropyl iodide as the oxidant. The method has a broad scope and shows high functional group compatibility. Toluene derivatives can be used as the coupling partner in an unreactive solvent.
- Aihara, Yoshinori,Tobisu, Mamoru,Fukumoto, Yoshiya,Chatani, Naoto
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supporting information
p. 15509 - 15512
(2014/12/11)
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- Nickel-catalyzed direct alkylation of C-H bonds in benzamides and acrylamides with functionalized alkyl halides via bidentate-chelation assistance
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The alkylation of the ortho C-H bonds in benzamides and acrylamides containing an 8-aminoquinoline moiety as a bidentate directing group with unactivated alkyl halides using nickel complexes as catalysts is described. The reaction shows high functional group compatibility. In reactions of meta-substituted aromatic amides, the reaction proceeds in a highly selective manner at the less hindered C-H bond.
- Aihara, Yoshinori,Chatani, Naoto
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supporting information
p. 5308 - 5311
(2013/05/21)
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- Palladium-catalyzed direct ortho -alkynylation of aromatic carboxylic acid derivatives
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The palladium-catalyzed direct alkynylation of C-H bonds in aromatic carboxylic acid derivatives is described. The use of 8-aminoquinoline as a directing group facilitates the alkynylation of an electronically diverse range of C(sp2)-H bonds.
- Ano, Yusuke,Tobisu, Mamoru,Chatani, Naoto
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supporting information; experimental part
p. 354 - 357
(2012/03/09)
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- Classical and three-dimensional QSAR for the inhibition of [ 3H]ponasterone a binding by diacylhydrazine-type ecdysone agonists to insect Sf-9 cells
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The activity of 52 diacylhydrazine congeners was evaluated by measuring the inhibition of the incorporation of [3H]ponasterone A into intact Sf-9 cells. Eleven compounds were newly synthesized in this study. Results showed that the substitution of the 2-CH3 or 3-OCH3 moiety of methoxyfenozide with other groups or the removal of either group was unfavorable to the activity. The activity was quantitatively analyzed using both classical QSAR (Hansch-Fujita) and three-dimensional QSAR methods (comparative molecular field analysis, CoMFA). Sterically favorable fields were observed at the 3- and 4-positions of the benzene ring opposite from the t-butyl group (B-ring), and a sterically unfavorable field was evidenced at the 2-position. Another sterically unfavorable field developed surrounding the favorable field observed at the 4-position of the B-ring. Electrostatically negative fields were observed near the CO moiety, above the benzene ring, and at the 4-position of the B-ring. The optimum hydrophobicity of compounds in terms of their log P values was calculated to be ≈4.1. Results of the three dimensional structure-activity relationship analyses were consistent with those obtained from the previously reported classical QSAR for 2-chlorobenzoyl analogs containing various para-substituents. The high activity of potent insecticides such as tebufenozide and chromafenozide were rationalized by CoMFA. Thus, this CoMFA result will be useful in the design of new compounds and in understanding the molecular mechanism of the ligand-receptor interactions.
- Nakagawa, Yoshiaki,Takahashi, Kaoru,Kishikawa, Hidetoshi,Ogura, Takehiko,Minakuchi, Chieka,Miyagawa, Hisashi
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p. 1333 - 1340
(2007/10/03)
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- Process to prepare 3-acyloxy-2-methyl-benzoic acid
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Die Erfindung betrifft ein verbessertes Verfahren zur Herstellung von 3-Acyloxy-2-methylbenzoes?uren durch Erhitzen von substituierten Naphthalinen in Gegenwart von Alkalimetallhydroxiden und anschlie?ender Acylierung.
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- Method of making a HIV-Protease inhibitor
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The present invention is directed to a method of making the HIV-protease inhibitor nelfinavir mesylate.
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Page/Page column 23-24
(2010/11/30)
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- Process for producing amide derivatives and intermediates therefor
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PCT No. PCT/JP96/02756 Sec. 371 Date Apr. 14, 1998 Sec. 102(e) Date Apr. 14, 1998 PCT Filed Sep. 24, 1996 PCT Pub. No. WO97/11937 PCT Pub. Date Apr. 3, 1997A method for producing an amide derivative of the formula [XV] wherein each symbol is as defined in the specification, and an enantiomer thereof, a novel intermediate useful for producing said compound and a production method thereof. The production method of the present invention is extremely easy and simple as compared to the conventional methods, and enables effective production of compound [XV] at high yields, which includes compound [XVI] having an HIV protease inhibitory action. In addition, the novel intermediates of the present invention are extremely useful as intermediates for producing not only the aforementioned compound [XVI] but also compounds useful as X-ray contrast media.
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- Process for the preparation of 3-acetoxy-2-methylbenzoyl chloride
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The present invention relates to a process for the preparation of 3-acetoxy-2-methylbenzoyl chloride by reacting an alkali metal salt of 3-aminonaph-thalene-1,5-disulfonic acid with alkali metal hydroxide and water in the weight ratio 1:(1 to 1.6):(1 to 1
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