15563-16-3Relevant academic research and scientific papers
Radical on Water Addition to the C=N Bond of Hydrazones: A Synthesis of Isoindolinone Derivatives
Nam, Tae Kyu,Jang, Doo Ok
, p. 7373 - 7379 (2018)
A radical on water addition to the C=N bond of hydrazones has been described. Hydrazone, diphenylsilane, alkyl iodide, and triethylborane afforded the corresponding addition products on water in good yields. A significant solvent effect was observed from the water. The developed protocol can be applied to the synthesis of 3-substituted isoindolinone derivatives. Moreover, the process offers environmentally benign tin-free radical reaction conditions.
Boron Chelates Derived from N-Acylhydrazones as Radical Acceptors: Photocatalyzed Coupling of Hydrazones with Carboxylic Acids
Dmitriev, Igor A.,Levin, Vitalij V.,Dilman, Alexander D.
, p. 8973 - 8977 (2021/11/24)
Difluoroboryl complexes obtained from N-acyl hydrazones upon brief treatment with boron trifluoride and allylic silane serve as efficient acceptors of alkyl radicals. The reaction of the boryl chelates with carboxylic acids in the presence of an acridine-type photocatalyst leading to N-acyl hydrazides is described. The efficiency of addition at the C=N bond of the chelates is determined by the formation of a nitrogen-centered radical stabilized by the boron-containing heterocyclic ring.
Nickel-Catalyzed N-Alkylation of Acylhydrazines and Arylamines Using Alcohols and Enantioselective Examples
Yang, Peng,Zhang, Caili,Ma, Yu,Zhang, Caiyun,Li, Aijie,Tang, Bo,Zhou, Jianrong Steve
supporting information, p. 14702 - 14706 (2017/10/20)
A borrowing-hydrogen reaction between amines and alcohols is an atom-economic way to prepare alkylamines, ideally with water as the sole byproduct. Herein, nickel catalysts are used for direct N-alkylation of hydrazides and arylamines using racemic alcohols. Moreover, a nickel catalyst of (S)-binapine was used for an asymmetric N-alkylation of benzohydrazide with racemic benzylic alcohols.
Preparation of optically active hydrazines and amines
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, (2008/06/13)
A process for the asymmetric hydrogenation of N-acylhydrazones to optically active N-acylhydrazines in the presence of a chiral phospholane catalyst complex, a process for the reductive N--N bond cleavage of N-acylhydrazine to amines with samarium diiodide, and a multistep process for converting keto group-bearing compounds to the corresponding optically active amino group-bearing compounds are disclosed.
