- Iron-catalysed sequential reaction towards α-aminonitriles from secondary amines, primary alcohols and trimethylsilyl cyanide
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We have developed a one-pot iron-catalysed sequential reaction of secondary amines with primary alcohols, trimethylsilyl cyanide and TBHP under mild reaction conditions to give the corresponding α-aminonitriles.
- Shen, Hang,Hu, Liangzhen,Liu, Qing,Hussain, Muhammad Ijaz,Pan, Jing,Huang, Mingming,Xiong, Yan
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- One-Pot Synthesis of α-Amino Nitrile Units through Alkylative Strecker Cyanation from Formamides
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In this work, we describe the one-pot synthesis of α-amino nitrile units by the concomitant addition of alkyl (or aryl) Grignard reagents and TMS cyanide through alkylative Strecker cyanation from readily available formamides. The reaction is broad in sco
- Yu, Bao,Bodinier, Florent,Saague-Tenefo, Maximiliene,Gerardo, Patrice,Ardisson, Janick,Lannou, Marie-Isabelle,Sorin, Geoffroy
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p. 3634 - 3640
(2021/07/22)
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- Covalently hooked EOSIN-Y in a Zr(IV) framework as visible-light mediated, heterogeneous photocatalyst for efficient C–H functionalization of tertiary amines
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Herein, we report the synthesis of a novel heterogeneous photo-catalyst by utilizing post-synthetic modification of an amine functionalized Zr(IV) metal-organic framework (UiO-66-NH2) through covalent hooking of EOSIN-Y via dehydrating coupling. The characterization of the catalyst was accomplished by FT-IR, XRD, BET surface analysis, TGA, as well as TEM, SEM, XPS, DRS-UV–visible, and NMR spectroscopy, confirming successful covalent linking of EOSIN-Y with the pendent –NH2 functionality in the framework. That post-modified EY@UiO-66-NH2 acts as simple and green visible light mediated photo-catalyst for the C–H activation of tertiary amines with excellent yields. Importantly, the activity of dye incorporated heterogeneous photo-catalyst is found superior to that for the homogeneous photo-catalyst EOSIN-Y. Thus, separation difficulty of homogeneous catalysis, as well as the environmental adverse effects of toxic EOSIN-Y can be excluded by developing such photo-catalyst. Moreover, EY@UiO-66-NH2 catalyst could be consistently recycled up to 10 cycles, without any significant loss in activity. Based on literature report and experimental findings, we also propose a plausible mechanism for the reaction.
- Kumar, Gaurav,Solanki, Pratik,Nazish, Mohd,Neogi, Subhadip,Kureshy, Rukhsana I.,Khan, Noor-ul H.
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p. 298 - 304
(2019/02/26)
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- Alpha-aminonitrile synthetic method
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The invention discloses a one-pot alpha-aminonitrile synthetic method and belongs to the technical field of organic chemistry synthesis. Various benzene ring halogen substituted or nitrogen alkyl or aryl substituted secondary amine, fatty alcohol and aromatic alcohol are taken as raw materials, peroxide is taken as the oxidizing agent, trimethylsilyl cyanide is taken as the nucleophilic cyaniding reagent, various kinds of molysite are taken as the catalyst, and one-step oxidation-condensation-nucleophilic reaction, concentration and purification are conducted in a solvent at room temperature or under the heating condition to generate a finished product. The method has certain universality, reaction conditions are mild, requirements for production equipment are low, technology is simple, raw materials are easy to obtain, and popularization is easy. By the adoption of the method, high-yield and high-quality alpha-aminonitrile can be prepared. The method can be widely applied to industrial production of alpha-aminonitrile. The prepared alpha-aminonitrile can be widely applied to synthesis of bioactive compounds or functional materials including alpha-amino acid, 1,2-diamine, tetrahydroquinoline, alpha-amino-aldehyde, ketone or beta-amino alcohol and has broad market application prospects.
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Paragraph 0055; 0062; 0064
(2017/01/19)
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- Ruthenium-catalyzed oxidative cyanation of tertiary amines with hydrogen peroxide and sodium cyanide
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(Chemical Equation Presented) Versatile intermediates for the synthesis of N-aryl-α-amino acids and N,N-disubstituted 1,2-diamines can now be synthesized with high efficiency by the ruthenium-catalyzed oxidative cyanation of tertiary amines. The use of hy
- Murahashi, Shun-Ichi,Komiya, Naruyoshi,Terai, Hiroyuki
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p. 6931 - 6933
(2007/10/03)
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- Process for the preparation of mono-N-β-cyanoethylanilines
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A new process for the preparation of mono-N-β-cyanoethylanilines, characterized in that a substituted or unsubstituted aniline compound is reacted with acrylonitrile in the presence of active bleaching earth as catalyst at a temperature of between 80° and 200° C. in a nonaqueous reaction medium.
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- 2-(N-Methylanilino)-2-phenylsulfanylacetonitrile, A Reagent Tested for Electrophilic, Nucleophilic, and Radical Reactions
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2-(N-Methylanilino)-2-phenylsulfanylacetonitrile 1 has been readily prepared from 2-(N-methylanilino)acetonitrile and diphenyl disulfide.Alkylation of the anion of 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated α-aminoalkenenitriles of 2E-configuration.Autoxidation of 1 in the presence of alkoxide ions afforded alkyl N-methyl-N-phenylcarbamates.Nucleophilic substitution of 1 with Grignard reagent or appropriate silyl compounds were promoted by CuI or Lewis acids to give varied α-amino nitriles.The 4-oxo-2-aminonitriles 9 obtained by condensation of 1 and titanium enolates can be considered as derivatives of 1,3-dicarbonyl compounds with the aldehyde group being activated to give an amino nitrile umpolung.When 1 was treated with tributylstannane, the corresponding amino nitrile α-radical was formed and the self-coupling product was isolated.
- Chen, Chih-Cheng,Chen, Same-Ting,Chuang, Tsung-Hsun,Fang, Jim-Min
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p. 2217 - 2222
(2007/10/02)
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- Rubine disazo acid dyes for polyamides
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Dyes of the formula STR1 wherein B and D are each independently 1,4-phenylene or 1,4-naphthylene; M is hydrogen, lithium, sodium, potassium or ammonium; A1 is hydrogen, C1-4 alkoxy, C1-4 alkyl, trifluoromethyl, nitro, chloro, bromo, cyano, or hydroxy; B1 and B2 are each hydrogen, C1-3 alkoxy, C1-3 alkyl, chloro or bromo; D1 is hydrogen, C1-4 alkoxy, C1-4 alkyl, or chloro; D2 is hydrogen, C1-4 alkoxy, C1-4 alkyl, chloro, bromo, fluoro, or acylamino, acyl being C1-5 alkanoyl, C1-5 alkylsulfonyl, benzoyl or benzenesulfonyl, each acyl unsubstituted or substituted with 1 to 3 of C1-2 alkyl, C1-2 alkoxy, chloro, bromo, cyano, or hydroxy; and R1 and R2 are each C1-6 alkyl, C1-6 chloro or bromoalkyl, C2-6 hydroxy- or dihydroxyalkyl, C2-6 alkoxyalkyl, C1-6 cyanoalkyl, or phenyl-C1-2 alkyl (phenyl unsubstituted or substituted with 1 to 3 of C1-2 alkyl, C1-2 alkoxy, chloro, bromo, cyano or hydroxy) are useful in dyeing natural and synthetic polyamide fibers in deep and level shades of red to blue.
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