88486-03-7Relevant academic research and scientific papers
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
Cyano-borrowing: Titanium-catalyzed direct amination of cyanohydrins with amines and enantioselective examples
Li, Qian,Li, Qing-Hua,Li, Wan-Fang,Li, Zhao-Feng,Liu, Tang-Lin,Peng, Yun-Gui,Ren, Li-Qing,Tao, Jing
supporting information, p. 651 - 654 (2020/01/28)
The direct amination of cyanohydrins with amines via a catalytic cyano-borrowing reaction was developed. The transformation features broad substrate scope, excellent functional group compatibility, and very mild and simple operations. Moreover, a titanium
Phosphine-Catalyzed Sequential Michael Addition between α-Aminonitriles and Methyl Acrylate for Cyclization: Synthesis of N-Aryl-Substituted Pyrrolidines
Jang,Sin,Paek,Jang,Jong
, p. 2228 - 2235 (2021/02/09)
Abstract: N-Aryl-substituted pyrrolidine derivativeswere synthesized via tributylphosphine-catalyzed sequential Michael addition ofα-aminonitriles and methyl acrylate as starting materials. The first Michaeladdition between α-aminonitrile and methyl acryl
An in-based 3D metal-organic framework as heterogeneous Lewis acid catalyst for multi-component Strecker reactions
Chai, Juan,Zhang, Ping,Xu, Jianing,Qi, Hui,Sun, Jing,Jing, Shubo,Chen, Xiaodong,Fan, Yong,Wang, Li
, p. 165 - 171 (2018/05/07)
A novel three-dimensional metal-organic framework (MOF) {[In3(NIPH)3 (HNIPH)(OH)2]·4H2O}n (1) (H2NIPH = 5-nitroisophthalic acid) with one-dimensional channels was synthesized and structurally characterized. Importantly, it demonstrates excellent catalytic activity for the Strecker reactions of two or three components under mild conditions. Moreover, the catalytic recycling of 1 as a representative example was explored. It can be easily separated and reused for no less than five runs with more than 80% conversion yield in catalytic ability.
In situ generation of functionality in a reactive binicotinic-acid-based ligand for the design of multi-functional copper(ii) complexes: Syntheses, structures and properties
Deng, Dongsheng,Guo, Hui,Kang, Guohui,Ma, Lufang,He, Xu,Ji, Baoming
, p. 1871 - 1880 (2015/03/04)
Under hydrothermal conditions, including tuning the reaction ratio and reaction temperature, three-dimensional (3D) porous {[Cu3(hbpdc)(OH)2(H2O)]·2H2O} (1), two-dimensional (2D) sheet {Cu2(hbpdc)(Hs
Vanadium-catalyzed oxidative Strecker reaction: α-C-H cyanation of para-methoxyphenyl (PMP)-protected primary amines
Chen, Chuo,Zhu, Chen,Xia, Ji-Bao
supporting information, p. 232 - 234 (2014/01/06)
We describe an oxidative Strecker reaction that allows for direct cyanation of para-methoxyphenyl (PMP)-protected primary amines. A vanadium(V) complex was used as the catalyst and TBHP as the oxidant. The cyanation occurs at the α-C position bearing either an alkyl or an aromatic group. This method provides a direct access to α-aminonitrile from amines with one-carbon extension.
Strecker-type reaction catalyzed by carboxylic acids in aqueous media
Xie, Zhengfeng,Li, Guilong,Zhao, Gang,Wang, Jide
experimental part, p. 2035 - 2039 (2009/12/27)
Carboxylic acid catalyzed Strecker-type reactions were successfully carried out by simply mixing aldehydes, amines, tributyltin cyanide and carboxylic acid in aqueous media at room temperature, to afford α-aminonitriles in high yields. Georg Thieme Verlag
Organocatalytic activation of TMSCN by basic ammonium salts for efficient cyanation of aldehydes and imines
Raj, I. Victor Paul,Suryavanshi, Gurunath,Sudalai
, p. 7211 - 7214 (2008/03/11)
Basic ammonium salts act as highly effective catalysts for the cyanosilylation of aldehydes and in Strecker-type aminonitrile synthesis using TMSCN as cyanide source at 25 °C under extremely mild conditions, affording very good to excellent yields of silylated cyanohydrins and α-aminonitriles.
Cu(OTf)2 or Et3N-catalyzed three-component condensation of aldehydes, amines and cyanides: a high yielding synthesis of α-aminonitriles
Paraskar, Abhimanyu S.,Sudalai, Arumugam
, p. 5759 - 5762 (2007/10/03)
Copper(II) triflate or Et3N have been found to catalyze, under ambient conditions, the addition of a cyanide anion, such as trimethylsilyl cyanide or acetone cyanohydrin, onto in situ generated imines, furnishing α-aminonitriles in excellent yi
