5766-79-0Relevant academic research and scientific papers
Electrochemically promoted oxidative α-cyanation of tertiary and secondary amines using cheap AIBN
Cai, Tian-Cheng,Gui, Qing-Wen,Hu, Wenxia,Li, Qiang,Liu, Xiaoying,Teng, Fan,Wang, Xiaoli,Xiong, Zhi-Yuan,Yu, Jialing
supporting information, p. 8254 - 8258 (2021/10/12)
The electrochemical α-cyanation of tertiary and secondary amines has been developed by using a cheap cyanide reagent, azobisisobutyronitrile (AIBN). The CN radical, generated throughn-Bu4NBr-meidated electrochemical oxidation, participates in a novel α-cyanation reaction under exogenous oxidant-free conditions.
One-Pot Synthesis of α-Amino Nitrile Units through Alkylative Strecker Cyanation from Formamides
Yu, Bao,Bodinier, Florent,Saague-Tenefo, Maximiliene,Gerardo, Patrice,Ardisson, Janick,Lannou, Marie-Isabelle,Sorin, Geoffroy
, p. 3634 - 3640 (2021/07/22)
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
A carbon dioxide-promoted three-component Strecker reaction
Fauziev, Ruslan V.,Ivanov, Roman E.,Kuchurov, Ilya V.,Zlotin, Sergei G.
, p. 10137 - 10144 (2021/12/24)
A three-component Strecker reaction of aldehydes, amines and KCN has been performed for the first time in supercritical carbon dioxide. In the proposed procedure, non-toxic and non-flammable carbon dioxide acts not only as an environmentally benign reaction medium but also as a reaction promoter via in situ formation of carbonic acid which provides a gradual release of the true cyanating agent (HCN) from available KCN. The reaction conditions (pressure, temperature, and concentrations of reagents) were optimized, and various aromatic and aliphatic amines and aldehydes were transformed into valuable α-amino nitriles including prospective pharmacological substances. The equimolar amount of used cyanogen reagent, carrying out the process in a sealed autoclave in a 'green' solvent medium under mild conditions (90 bar, 35 °C) along with the high yields of products and the scalability of the developed procedure make it suitable for sustainable industrial applications. This journal is
Strecker reactions with hexacyanoferrates as non-toxic cyanide sources
Grundke, Caroline,Opatz, Till
supporting information, p. 2362 - 2366 (2019/05/17)
The Strecker reaction is the most widely applied three-component reaction. Although highly useful for the preparation of α-amino nitriles, α-amino acids, hydantoins and numerous related compounds, the need for the application of toxic sources of HCN limits its application in both academic and industrial settings. Here, we present a facile protocol for Strecker reactions using a mixture of potassium ferri- and ferrocyanides as a non-toxic substitute.
A unique combination of KI/ZnFe2O4 as a catalyst for oxidative Strecker reaction
Ghandi, Leila,Kazemi Miraki, Maryam,Karimi, Meghdad,Radfar, Iman,Heydari, Akbar
, (2018/11/23)
α-Aminonitriles as key intermediates for the preparation of α-amino acid derivatives, amides, diamines, peptides, proteins and heterocycles were synthesized through methylarene oxidation in the Strecker reaction using a unique combination of KI/ZnFe2O4 as the best catalyst and aqueous tert-butyl hydroperoxide as oxidant. A wide range of amines and methylarenes were converted to the corresponding products. Operational simplicity, short reaction time and recyclability of the catalyst are advantages of this protocol.
Straightforward α-Amino Nitrile Synthesis Through Mo(CO)6-Catalyzed Reductive Functionalization of Carboxamides
Trillo, Paz,Slagbrand, Tove,Adolfsson, Hans
, p. 12347 - 12351 (2018/09/10)
The selective reduction of amides into an intermediate hemiaminal catalyzed by Mo(CO)6 together with the inexpensive and easy to handle TMDS (1,1,3,3-tetramethyldisiloxane) as reducing agent, followed by subsequent trapping of the hemiaminal with a cyanide source, allows for the straightforward synthesis of α-amino nitriles. The methodology presented here, displays high levels of chemoselectivity allowing for the reduction of amides in the presence of functional groups such as ketones, imines, aldehydes, and acids, which affords a simple route for the synthesis of α-amino nitriles with a broad scope of functionalities in high yields. Furthermore, the applicability of this methodology is demonstrated by scale up experiments and by derivatization of the target compounds into synthetically interesting products. The selective cyanation is successfully applied in late stage functionalizations of amide containing drugs and prolinol derivatives.
Magnetically separable g-C3N4 hybrid nanocomposite: Highly efficient and eco-friendly recyclable catalyst for one-pot synthesis of α-aminonitriles
Azizi, Najmedin,Farhadi, Elham
, (2017/12/28)
A magnetically separable graphitic carbon nitride nanocomposite (Fe3O4/g-C3N4) as a catalyst for the three-component condensation reactions of carbonyl compounds, amines and trimethylsilylcyanide was thoroughly investigated. The reaction of these three components was found to be efficient, economical and green and took place in the presence of a catalytic amount of the magnetically separable catalyst to yield the corresponding α-aminonitriles in good to excellent yields. The prepared nanocomposite was characterized using scanning electron microscopy and energy-dispersive X-ray and Fourier transform infrared spectroscopies. The nanocomposite was also found to be reusable could be recovered easily and reused several times without distinct deterioration in its catalytic activity.
Expeditious and efficient synthesis of Strecker's α-aminonitriles catalyzed by sulfated polyborate
Indalkar, Krishna S.,Khatri, Chetan K.,Chaturbhuj, Ganesh U.
supporting information, p. 2144 - 2148 (2017/05/10)
A straightforward, mild, efficient, and environmentally benign protocol for a three-component Strecker reaction of aldehydes or ketones, amines, and trimethylsilyl cyanide catalyzed by sulfated polyborate has been described to afford α-aminonitriles under solvent-free reaction conditions. The major advantages of the present method are excellent yields, shorter reaction time, simple experimental procedure, easy workup procedure, recyclability of the catalyst, solvent-free reaction conditions and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards.
Mechanochemical Strecker Reaction: Access to α-Aminonitriles and Tetrahydroisoquinolines under Ball-Milling Conditions
Hernández, José G.,Turberg, Mathias,Schiffers, Ingo,Bolm, Carsten
supporting information, p. 14513 - 14517 (2016/10/03)
A mechanochemical version of the Strecker reaction for the synthesis of α-aminonitriles was developed. The milling of aldehydes, amines, and potassium cyanide in the presence of SiO2gave the corresponding α-aminonitriles in good to high yields. The high efficiency of the mechanochemical Strecker-type multicomponent reaction allowed the one-pot synthesis of tetrahydroisoquinolines after a subsequent internal N-alkylation reaction.
Propylphosphonic anhydride (T3P) catalyzed one-pot synthesis of α-aminonitriles
Reddy, Sirigireddy Sudharsan,Reddy, Bhoomireddy Rajendra Prasad,Reddy, Peddiahgari Vasu Govardhana
, p. 739 - 743 (2015/08/03)
Abstract The Strecker reaction was performed via a one-pot three component condensation of hetero aromatic/aromatic aldehydes, secondary amines and trimetylsilyl cyanide in the presence of propylphosphonic anhydride (T3P) to accomplish the corresponding α-aminonitriles. The main advantages of this method are very short reaction time and excellent yields.
