36271-19-9Relevant academic research and scientific papers
A new and convenient synthesis of antazoline derivatives
Dash,Kudav,Parihar
, p. 401 - 404 (2006)
Different N-benzyl anilines were N-alkylated with chloroacetonitrile to give the corresponding nitriles, which were subsequently condensed with ethylenediamine in the presence of thioacetamide to afford the corresponding title antazoline derivatives.
Iron-catalyzed reductive strecker reaction
Yan, Fachao,Huang, Zijun,Du, Chen-Xia,Bai, Jian-Fei,Li, Yuehui
, p. 188 - 194 (2021/02/03)
Strecker reaction is widely applied for the synthesis of amino acids from aldehydes, amines and cyanides. Herein, we report the FeI2-catalyzed reductive Strecker type reaction of formamides instead of aldehydes to produce amino acetonitriles. The challenging capture of carbinolamine intermediates by CN? was achieved via Fe catalysis. This approach afforded better yields than the use of Ir- or Rh-catalysts. The application ability of this methodology is demonstrated by 1) one-pot construction of (13C labeled) complex molecules from CO2 via amino acetonitrile intermediates and 2) convenient production of homologated carboxylic acids from aldehydes.
Iron-catalysed carbene-transfer reactions of diazo acetonitrile
Empel, Claire,Hock, Katharina J.,Koenigs, Rene M.
supporting information, p. 7129 - 7133 (2018/10/24)
A continuous-flow protocol for the synthesis of diazo acetonitrile was developed. It was further applied in iron-catalysed insertion reactions of diazo acetonitrile into N-H and S-H bonds to yield valuable α-substituted acetonitrile, including gram-scale synthesis.
Iron-catalysed sequential reaction towards α-aminonitriles from secondary amines, primary alcohols and trimethylsilyl cyanide
Shen, Hang,Hu, Liangzhen,Liu, Qing,Hussain, Muhammad Ijaz,Pan, Jing,Huang, Mingming,Xiong, Yan
supporting information, p. 2776 - 2779 (2016/02/19)
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.
Alpha-aminonitrile synthetic method
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Paragraph 0055; 0062; 0064, (2017/01/19)
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.
Preparation method for alpha-cyanoamine
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Paragraph 0054; 0055, (2016/10/07)
The invention discloses a preparation method for alpha-cyanoamine. According to the method, the product alpha-cyanoamine is prepared through nucleophilic substitution in a mixed solvent in the presence of an oxidizing agent with an amine compound and cyanoacetic acid as reactants, iodide as a catalyst and sodium acetate as alkali. The catalyst used in the method has high reactivity; reaction conditions are mild; the application scope of a substrate is wide; post-treatment is convenient; the yield of the target product is high; preparation process is simple, green and environment-friendly; and used raw materials are widely available.
Cyanoacetic Acid as a Masked Electrophile: Transition-Metal-Free Cyanomethylation of Amines and Carboxylic Acids
Wang, Hongxiang,Shao, Ying,Zheng, Hao,Wang, Hanghang,Cheng, Jiang,Wan, Xiaobing
supporting information, p. 18333 - 18337 (2015/12/24)
Using cyanoacetic acid as a masked electrophile, a new cyanomethylation reaction of amines and carboxylic acids was developed, producing a variety of α-aminonitriles and cyanomethyl esters with good yields and excellent functionality tolerance. This protocol features simple manipulation, inexpensive reagents, and a wide substrate scope. Iodoacetonitrile was generated in situ from the iodination-decarboxylation of cyanoacetic acid in this transformation.
Potassium ion cationized polyether cyanide [K+{PEG}CN-] as a novel cyanide source for oxidative cyanation of tertiary amines
Panwar, Vineeta,Ray, Siddharth S.,Jain, Suman L.
, p. 4184 - 4186 (2015/06/22)
Potassium ions cationized polyether cyanide [K+{PEG}CN-] was readily synthesized by mixing potassium cyanide and PEG400 at room temperature and used as a cost effective and comparatively safer alternative to the toxic sodium cyanide/acetic acid system for generating in situ HCN for the oxidative cyanation of tertiary amines with hydrogen peroxide using RuCl3 as catalyst. This method affords a facile approach to the synthesis of α-aminonitriles in high yields under solvent-free and acid-free reaction conditions.
Iron-catalyzed generation of α-amino nitriles from tertiary amines
Wagner, Alexander,Han, Wei,Mayer, Peter,Ofial, Armin R.
, p. 3058 - 3070 (2014/03/21)
The use of iron(II) chloride as catalyst, trimethylsilyl cyanide as source of cyanide ions, and tert-butyl hydroperoxide as oxidant enabled the conversion of aromatic, benzylic, and aliphatic tertiary amines into α-Amino nitriles under mild conditions. Chemoselective functionalization of N-CH3 to N-CH2CN was achieved in the presence of Nbenzyl and N-alkyl groups. N,N-Dialkylanilines, PhNR2, with R=Et, Bu, Bn furnished the alkyl-(aryl)aminoacetonitriles PhN(R)CH2CN as the main products accompanied by α-Amino nitriles generated by ordinary a-cyanation of the aniline PhNR2. Formation of PhN(R)CH2CN was rationalized by oxidative degradation of N,N-dialkylanilines to N-alkylanilines, their condensation with formaldehyde, generated by oxidation of the solvent methanol, and final trapping of the thus formed iminium ions by cyanide.
Agents for the treatment of overactive detrusor. IV. Synthesis and structure-activity relationships of cyclic analogues of terodiline
Take,Okumura,Tsubaki,Terai,Shiokawa
, p. 507 - 515 (2007/10/02)
A series of pyrrolidine derivatives were synthesized and examined for inhibitory activity on detrusor contraction in vivo. Among those compounds, 5,5-dimethyl-2-(2,2-diphenylethyl)-3-isopropylidenepyrrolidine hydrochloride (41 · HCl), 2-(2,2-di(4-fluorophenyl)ethylene)-5,5-dimethyl-3-isopropylidenepyrrol idine hydrochloride (42 · HCl), (+)5,5-dimethyl-2-(N,N-diphenylaminomethyl)-3-isopropylidenepyrrolidin e hydrochloride (+)-(43a · HCl),(-)-5,5-dimethyl-2-(N,N-diphenylaminomethyl)-3-isopropylidenepyrr olidine hydrochloride (-)-(43a · HCl), and 2-(N,N-di(4-fluorophenyl)aminomethyl)-5,5-dimethyl-3-isopropylidenepyr rolidine methanesulfonate (43b · MsOH) showed stronger inhibitory activity on detrusor contraction than terodiline.
