882-36-0Relevant articles and documents
Nickel-promoted oxidative domino Csp3-H/N-H bond double-isocyanide insertion reaction to construct pyrrolin-2-ones
Wen, Li-Rong,Wang, Ning-Ning,Du, Wu-Bo,Ma, Qiang,Zhang, Lin-Bao,Li, Ming
supporting information, p. 2895 - 2900 (2021/04/14)
The first nickel-catalyzed oxidative domino Csp3-H/N-H double isocyanide insertion reaction of acetamides with isocyanides has been developed for the synthesis of pyrrolin-2-one derivatives. A wide range of acetamides bearing various functional groups are compatible with this reaction system by utilizing Ni(acac)2as a catalyst. In this transformation, isocyanide could serve as a C1 connector and insert into the inactive Csp3-H bond, representing an effective way to construct heterocycles.
HFIP-mediated strategy towards β-oxo amides and subsequent Friedel-Craft type cyclization to 2?quinolinones using recyclable catalyst
Kabi, Arup K.,Gujjarappa, Raghuram,Vodnala, Nagaraju,Kaldhi, Dhananjaya,Tyagi, Ujjawal,Mukherjee, Kalisadhan,Malakar, Chandi C.
supporting information, (2020/10/20)
A simple and cost-effective 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-mediated protocol for the synthesis of β-oxo amides has been described by using amines and β-keto esters as substrates. The reaction conditions were found to be highly efficient towards the cleavage of C[sbnd]O bond and consequent formation of the products in excellent yields and selectivity. The obtained β-oxo amides were further transformed in to the synthetically useful 2?quinolinones via intramolecular Friedel-Craft type cyclization of aromatic ring using ferrites as a recyclable catalyst. A spectrum of substrates bearing broad range of functional groups were well tolerated under the reaction conditions. The proposed mechanistic pathways were substantially verified by literature and mass-spectroscopic evidences.
Synthesis of α-Alkyl-β-Hydroxy Amides through Biocatalytic Dynamic Kinetic Resolution Employing Alcohol Dehydrogenases
Méndez-Sánchez, Daniel,Mourelle-Insua, ángela,Gotor-Fernández, Vicente,Lavandera, Iván
supporting information, p. 2706 - 2712 (2019/05/10)
Chiral (α-substituted) β-hydroxy amides are interesting derivatives as they are useful building blocks of many biologically active compounds. Herein, the biocatalytic stereocontrolled synthesis of various acyclic syn-α-alkyl-β-hydroxy amides through a dynamic kinetic resolution is shown. Hence, a series of overexpressed alcohol dehydrogenases (ADHs) in Escherichia coli was used to reduce the corresponding racemic β-keto amides. Among them, ADH-A from Rhodococcus ruber and commercial evo-1.1.200 afforded the best activities and selectivities, giving access to the opposite enantiomers with high diastereomeric excess and excellent enantiomeric excess. Some of these compounds were obtained at semipreparative scale. (Figure presented.).
