4355-46-8Relevant academic research and scientific papers
Primary α-tertiary amine synthesis via α-C-H functionalization
Vasu, Dhananjayan,Fuentes de Arriba, Angel L.,Leitch, Jamie A.,De Gombert, Antoine,Dixon, Darren J.
, p. 3401 - 3407 (2019/03/21)
A quinone-mediated general synthetic platform for the construction of primary α-tertiary amines from abundant primary α-branched amine starting materials is described. This procedure pivots on the efficient in situ generation of reactive ketimine intermediates and subsequent reaction with carbon-centered nucleophiles such as organomagnesium and organolithium reagents, and TMSCN, creating quaternary centers. Furthermore, extension to reverse polarity photoredox catalysis enables reactivity with electrophiles, via a nucleophilic α-amino radical intermediate. This efficient, broadly applicable and scalable amine-to-amine synthetic platform was successfully applied to library and API synthesis and in the functionalization of drug molecules.
Titanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia
Li, Qing-Hua,Li, Zhao-Feng,Tao, Jing,Li, Wan-Fang,Ren, Li-Qing,Li, Qian,Peng, Yun-Gui,Liu, Tang-Lin
supporting information, p. 8429 - 8433 (2019/10/14)
α-Aminonitrile was an important building block in natural products and key intermedia in organic chemistry. Herein, the direct amination of cyanohydrins with the partner of ammonia to synthesis N-unprotected α-aminonitriles is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesis with moderate to high yields under mild reaction conditions.
New enzymatic methods for the synthesis of primary α-aminonitriles and unnatural α-amino acids by oxidative cyanation of primary amines with d-amino acid oxidase from porcine kidney
Kawahara, Nobuhiro,Yasukawa, Kazuyuki,Asano, Yasuhisa
supporting information, p. 418 - 424 (2017/08/14)
Oxidation of amino groups in amines or amino acids activates the sp3 Cα-H bond to form imines, making the alpha carbon atom a preferable target for nucleophilic reagents such as cyanide. Therefore, we focused on the oxidase reaction for the production of primary α-aminonitriles via imines. d-Amino acid oxidase from porcine kidney (pkDAO) and l-amino acid oxidase from Crotalus atrox catalyzed the synthesis of 2-amino-2-cyano-3-phenylpropanoic acid from phenylalanine and potassium cyanide (KCN). Mutant pkDAO (Y228L/R283G) catalyzed the synthesis of racemic-2-methyl-2-phenylglycinonitrile from (R)-α-methylbenzylamine and KCN. Based on these results, we developed a new cascade reaction for the synthesis of unnatural α-amino acids from primary amines using mutant pkDAO and nitrilase AY487533. This is the first report of the enzymatic synthesis of primary α-aminonitriles and unnatural α-amino acids. These methods will contribute widely to the synthesis of primary α-aminonitriles and unnatural α-amino acids in aqueous systems.
Approaches to the construction of substituted 4-amino-1 H -pyrrol-2(5 H)-ones
Zali-Boeini, Hassan,Mobin, Mehdi,Hajibabaei, Khadijeh,Ghani, Maryam
experimental part, p. 5808 - 5812 (2012/07/31)
Fully substituted 4-aminopyrrolones are easily accessed via simple routes starting from imines, ketones, or α-bromophenyl acetonitriles. Imines were reacted with KCN/NH4Cl in aqueous ethanol to produce α-arylamino benzyl cyanides. On the other hand, ketones were transformed to the desired α-amino nitriles using a modified Strecker reaction. Then, α-amino nitrile precursors were allowed to react with a suitable acyl halide to produce the corresponding amides. Further treatment of these amides with ethanolic KOH converted them to highly substituted 4-amino-1H-pyrrol-2(5H)- one derivatives in moderate to excellent yields.
Process for the preparation of (schiff bases of)alpha-alkyl-alpha-amino acid amides
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Page column 3, (2008/06/13)
Process for the preparation of a Schiff base of an α-alkyl-α-amino acid amide and an aldehyde, wherein the corresponding α-aminonitrile is contacted with a base and the aldehyde and wherein it is ensured that the reagents are in good contact. The Schiff base obtained may be further hydrolysed to form the α-alkyl-α-amino acid amide and the aldehyde. Preferably a substituted or unsubstituted benzaldehyde is used as the aldehyde. The reaction is preferably carried out in a practically homogeneously mixed phase obtained by using a solvent, for example methanol or ethanol. Preferably NaOH or KOH is used as the base.
Process for the preparation of 4-oxoimidazolinium salts
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, (2008/06/13)
4-Oxoimidazolinium salts of the general formula: STR1 wherein R1 and R2 independently of one another are C1-10 -alkyl, C2-10 -alkenyl, C3-7 -cycloalkyl or optionally substituted aryl, arylalkyl, heteroaryl or heteroarylalkyl, or R1 and R2, together with the carbon atom to which they are bonded, form a three-membered to seven-membered saturated or unsaturated carbocyclic or heterocyclic ring, R3 is a C1-10 -alkyl group, C1-10 -alkenyl group, C3-7 -cycloalkyl group, aryl group, arylalkyl group or heteroaryl group, and A-- is an anion of a strong acid, are prepared by the cyclization of an α-acylaminonitrile in a nonaqueous solvent, in the presence of a lower alcohol and a strong acid. The compounds are intermediates for pharmaceutical active substances, for example, angiotensin II antagonists.
Useful Synthesis of α-Aminonitriles by Means of Alumina and Ultrasound
Hanafusa, Terukiyo,Ichihara, Junko,Ashida, Tetsuya
, p. 687 - 690 (2007/10/02)
Combined use of alumina and ultrasound facilitates the synthesis of α-aminonitriles under solid-liquid two phase conditions from carbonyl compounds, salts of amines and potassium cyanide in organic solvents.
