15190-14-4Relevant articles and documents
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
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.
Superparamagnetic iron oxide as an efficient catalyst for the one-pot, solvent-free synthesis of α-aminonitriles
Mojtahedi, Mohammad M.,Saeed Abaee,Alishiri, Tooba
experimental part, p. 2322 - 2325 (2009/09/06)
Superparamagnetic Fe3O4 is shown to act as a very efficient catalyst for the one-pot, three-component synthesis of α-aminonitriles from aldehydes, amines, and TMSCN. The catalyst is easily recovered by the use of an external magnet and reused in several reactions without any noticeable loss of activity. The products are obtained rapidly at room temperature in good purity upon separation of the catalyst and evaporation of the volatiles of the reaction mixture.
