- Domino Reaction for the Synthesis of Highly Functionalized Triazatricyclo[6.2.2.01,6]dodecane
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A simple and highly efficient protocol has been developed for the synthesis of triazatricyclo[6.2.2.01,6]dodecane-9,12-dione (TATCD) derivatives. Use of metal hydroxide catalyst in the presence of protic solvent plays a key role in these reaction transformations. Mechanistic studies specify that the proposed mechanism proceeds only via aldol reaction, condensation, cyclization, and dehydration to form the desired product. This current protocol provides several advantages such as use of a readily available precursor, consumption of less energy, short reaction time, moderate to good yields, and convenient workup. GRAPHICAL ABSTRACT.
- Ramachandran, Gunasekar,Sathiyanarayanan, Kulathu Iyer
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- Transfer Hydration of Dinitriles to Dicarboxamides
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We present a robust method for double transfer hydration of dinitriles to afford diamides. The transfer hydration of 1, n -dinitriles (n = 1-6) proceeds smoothly in the presence of a palladium(II) catalyst with acetamide as a water donor, affording the corresponding diamides in moderate to high yields, without involving significant side reactions such as monohydration or cyclization. The equilibrium was shifted in the forward direction by removing coproduced acetonitrile under reduced pressure.
- Naka, Hiroshi,Naraoka, Asuka
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- Corresponding amine nitrile and method of manufacturing thereof
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The invention relates to a preparation method of nitrile. Compared with the prior art, the preparation method has the characteristics of obvious reduction of the usage amount of ammonia sources, low environmental pressure, low energy consumption, low production cost, high purity and yields of nitrile products, and the like, and can be used for obtaining nitrile with a more complex structure. The invention also relates to a method for preparing corresponding amine with nitrile.
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Paragraph 0124; 0125; 0127
(2018/05/24)
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- Corresponding amine nitrile and method of manufacturing thereof (by machine translation)
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The present invention relates to a nitrile manufacturing method, which has characteristics of significantly-reduced ammonia source consumption, low environmental pressure, low energy consumption, low production cost, high nitrile purity, high nitrile yield and the like compared with the method in the prior art, wherein nitrile having a complicated structure can be obtained through the method. The present invention further relates to a method for producing a corresponding amine from the nitrile.
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Paragraph 0124; 0125; 0126; 0127
(2018/07/15)
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- Corresponding amine nitrile and method of manufacturing thereof
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The invention relates to a preparation method of nitrile. Compared with the prior art, the preparation method has the characteristics of obvious reduction of the usage amount of ammonia sources, low environmental pressure, low energy consumption, low production cost, high purity and yields of nitrile products, and the like, and can be used for obtaining nitrile with a more complex structure. The invention also relates to a method for preparing corresponding amine with nitrile.
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Paragraph 0125; 0126; 0127; 0128
(2018/07/15)
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- Modulation of Nitrile Hydratase Regioselectivity towards Dinitriles by Tailoring the Substrate Binding Pocket Residues
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The regioselective hydration of dinitriles is one of the most attractive approaches to prepare ω-cyanocarboxamides or diamides and such regioselectivity is often beyond the capability of chemical catalysts. The use of nitrile hydratase to biotransform dinitriles selectively would be highly desirable. Molecular docking of two aliphatic dinitriles and two aromatic dinitriles into the active site of a nitrile hydratase (NHase) from Rhodococcus rhodochrous J1 allowed the identification of proximal NHase substrate binding pocket residues. Four residues (βLeu48, βPhe51, βTyr68, and βTrp72) were selected for single- and double-point mutations to modulate the NHase regioselectivity towards dinitriles. Several NHase mutants with an altered regioselectivity were obtained, and the best one was Y68T/W72Y. Docking experiments further indicated that the poor binding affinity of aliphatic and aromatic ω-cyanocarboxamides to the NHase variants resulted in distinct regioselectivity between wild-type and mutated NHases.
- Cheng, Zhongyi,Cui, Wenjing,Xia, Yuanyuan,Peplowski, Lukasz,Kobayashi, Michihiko,Zhou, Zhemin
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p. 449 - 458
(2017/12/15)
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- Methanol or formaldehyde ammoxidizing method of synthesizing amide
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The invention relates to a methanol or formaldehyde ammoxidizing the method of synthesizing amide. Using methanol or formaldehyde, ammonia and air as the raw materials, in 1-3 gas reactor is continuously carried out in a catalytic reaction, synthesis (C-C) is provided with a carbon-carbon single bond or carbon-carbon-carbon single bond amide (C-C-C) organic compound (called C 2 or C 3 amide, mainly hydroxy acetamide, amino acetamide, diglycolamidic amide, malonamide and nitrilo- three b amide).
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Paragraph 0039; 0040; 0041
(2016/10/09)
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- Mild and selective heterogeneous catalytic hydration of nitriles to amides by flowing through manganese dioxide
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A sustainable flow chemistry process for the hydration of nitriles, whereby an aqueous solution of the nitrile is passed through a column containing commercially available amorphous manganese dioxide, has been developed. The product is obtained simply by concentration of the output stream without any other workup steps. The protocol described is rapid, robust, reliable, and scalable, and it has been applied to a broad range of substrates, showing a high level of chemical tolerance.
- Battilocchio, Claudio,Hawkins, Joel M.,Ley, Steven V.
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supporting information
p. 1060 - 1063
(2016/10/17)
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- Anodic mediated synthesis and antifungal study of bis-1,3,4-oxadiazoles
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A novel, facile and eco-compatible electrochemical synthesis of substituted bis-1,3,4-oxadlazoles have been carried out at platinum electrode via controlled potential electrocyclization of methylenediacylthiosemicarbazones in the presence of acetonitrile as non-aqueous solvent and LiClO4 as supporting electrolyte. The reaction products were characterized by spectroscopic methods and mechanism was deduced from cyclic voltammetry. The synthesized compounds were screened for their antifungal activity against Candida albicans, Alternaria solani, Aspergillus niger and results have been compared with the standard antifungal drug Griseofulvin. Excellent yields with high atom economy, shortest reaction time and easy work-up are attractive features in context to green chemistry.
- Sharma,Saraswat,Singh,Siddiqui,Kehari,Singh
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p. 991 - 996
(2013/09/23)
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- A heterogeneous catalytic method for the conversion of nitriles into amides using molecular sieves modified with copper(II)
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A heterogenous catalytic method is developed for the hydration of nitriles into amides with acetaldoxime. Copper(II) supported on 4 molecular sieves is an efficient catalyst for this reaction.
- Kiss, árpád,Hell, Zoltán
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experimental part
p. 6021 - 6023
(2011/11/28)
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- Process for the synthesis and recovery of nitramines
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A method is provided for the synthesis of nitramines, and the recovery of the nitramines from a clathrate.
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- Selective conversion of nitriles to amides by Amberlyst A-26 supported hydroperoxide
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A mild, efficient and selective conversion of nitriles to amides is achieved by employing Amberlyst A-26 supported hydroperoxide, which is prepared in situ from hydrogen peroxide and Amberlyst A-26 (OH- form). Nitriles and dinitriles are transformed to their corresponding amides and diamides, respectively. Reactions proceed within 0.5-5 hr upon addition of a catalytic amount of Amberlyst A 26(OH-) to a methanolic solution of nitrile and hydrogen peroxide (35%), at room temperature.
- Mansour Lakouraj,Bahrami
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p. 974 - 975
(2007/10/03)
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- Substituted 2-acylamino-pyridines as inhibitors of nitric oxide synthase
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Substituted 2-acylaminopyridine compounds and pharmaceutically acceptable salts which have been found useful in the treatment of nitric oxide synthase mediated diseases and disorders.
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- Mild and efficient conversion of nitriles to amides with basic urea- hydrogen peroxide adduct
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The urea-hydrogen peroxide adduct, an inexpensive, stable and easily handled reagent has shown utility for mild and efficient transformation of nitriles into the corresponding aliphatic or aromatic amides. Reaction proceeds in aqueous acetone, within 0.5-2. 5h, in the presence of catalytic amount of K2CO3, at room temperature.
- Balicki,Kaczmarek
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p. 3149 - 3155
(2007/10/02)
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- Electrophilic Substitution in Malonamide. Evidence for Reaction via the Enol Tautomer
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The kinetics of the nitrosation, bromination and iodination of malonamide have been studied in water at 25 deg C.Throughout, reaction was first order in .At low acidity and relatively high , reactions were fully zero-order in and acid-catalysed.At higher acidity and lower reaction was first-order in and not now acid-catalysed.Similar first-order behaviour was found for bromination and nitrosation (by BrNO and ONSCN generated in situ).It was not possible by changing the reaction conditions to achieve the zero-order pattern with either bromination or nitrosation.The results are consistent with a mechanism involving reaction of the electrophile with an intermediate derived from MA which we suggest is the enol tautomer.For iodination either enolisation or reaction of the enol can be made rate-limiting.For enolisation the value of the rate constant ke (in Rate = ke+>) was found to be 3.3 * 10-3 dm3 mol-1 s-1.The results also suggest that I2, Br2, BrNO and ONSCN react with the enol at or close to the encounter controlled limit, enabling a value for KE (the equilibrium constant for enolisation) of (4 +/- 2) * 1010 to be obtained.The methylene protons in MA are readily exchanged with D from the solvent in an acid catalysed process.The enolisation of CD2(COND2)2 is slower than that of CH2(CONH2)2 by a factor of 2.3 and the deuterium solvent isotope effect is close to 1.The mechanism of enolisation of MA is discussed.
- Williams, D. Lyn H.,Xia, Ling
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p. 1429 - 1432
(2007/10/02)
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- SYNTHESIS AND STRUCTURE OF SUBSTITUTED 3,4-DIHYDROPYRIDIN-2-ONES
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The condensation of benzylideneacetoacetic ester with cyanoacetamide in the presence of triethylamine yielded 3-carbamoyl-3,4-dihydropyridin-2-one, while the condensation of arylidenecyanoacetamides with β-aminocrotonic ester in acetic acid yielded 3-cyano-3,4-dihydropyridin-2-ones.It was established by NMR spectroscopy that 3-cyano-4-R-5-ethoxycarbonyl-6-methyl-3,4-dihydropyridin-2-ones exist in solutions in the form of a mixture of cis- and trans-stereosiomers in a 10:1 ratio.
- Krauze, A. A.,Liepin'sh, E. E.,Kalme, Z. A.,Pelcher, Yu. E.,Dubur, G. Ya.
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p. 1241 - 1245
(2007/10/02)
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- Process for the preparation of vinylcyclopropane derivatives
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This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yield. For the process an alkylating agent and activated methylene compound are reacted in the presence of a cyclic polyether compound and alkali metal compound. Water can also be present and/or the reaction may be carried out in an inert organic diluent.
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- Process for the preparation of vinylcyclopropane derivatives
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This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yield. For the process an alkylating agent and activated methylene compound are reacted in the presence of an alkylene oxide derivative and alkali metal compound. Water can also be present and/or the reaction may be carried out in an inert organic diluent.
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- Process for the preparation of vinylcyclopropane derivatives
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This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yields. The process involves reacting an alkylating agent and an activated methylene compound in the presence of an onium compound, an alkali metal compound and water, which while only necessary in trace amounts can be present in substantial quantities.
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