5469-56-7Relevant articles and documents
One Amine–3 Tasks: Reductive Coupling of Imines with Olefins in Batch and Flow
Lefebvre, Quentin,Porta, Riccardo,Millet, Anthony,Jia, Jiaqi,Rueping, Magnus
supporting information, p. 1363 - 1367 (2020/02/04)
Owing to their wide range of biological properties, γ-aminobutyric acid derivatives (GABA) have been extensively studied and found noteworthy industrial applications. However, atom-economical and efficient processes for their production are scarce and would greatly benefit from further investigations. Herein, we demonstrate that an iridium-based photocatalyst promotes the direct reductive cross-coupling of imines with olefins upon irradiation with visible light to give GABA derivatives in good yields and selectivities. We also stress the enabling triple role of tributylamine additive in this process, discuss the advantages of strategies based on proton-coupled electron transfer (PCET) and demonstrate the scale-up of this reaction in continuous flow.
Reductive Amination/Cyclization of Keto Acids Using a Hydrosilane for Selective Production of Lactams versus Cyclic Amines by Switching of the Indium Catalyst
Ogiwara, Yohei,Uchiyama, Takuya,Sakai, Norio
supporting information, p. 1864 - 1867 (2016/02/03)
Described herein is that the catalytic construction of N-substituted five- and six-membered lactams from keto acids with primary amines by reductive amination, using an indium/silane combination. This relatively benign and safe catalyst/reductant system tolerates the use of a variety of functional groups, especially ones that are reduction-sensitive. A direct switch from synthesizing lactams to synthesizing cyclic amines is achieved by changing the catalyst from In(OAc)3 to InI3. This conversion occurs by further reduction of the lactam using the indium/silane pair.
Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: V. Cyclization of anilides of styrylacetic acids in polyphosphoric acid
Vas'Kevich,Vas'Kevich,Daniluk, I. Yu.,Vovk
, p. 1175 - 1181 (2013/10/01)
Anilides of styrylacetic acids at heating in polyphosphoric acid undergo an intramolecular cyclization giving 1,5-diarylpyrrolidin-2-ones, 5-aryl-1,3,4,5-tetrahydro-2H-benzazepin-2-ones, and 5-(3-fluorophenyl) dihydrofuran-2(3H)-one, where the ratio of th