78007-50-8Relevant academic research and scientific papers
Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds
Yang, Tonghao,Lin, Yajun,Yang, Chaoqun,Yu, Wei
supporting information, p. 6097 - 6102 (2019/11/20)
Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds provides a simple and atom-economical approach toward enamides and isoquinolones. This paper reports two catalyst systems for these transformations which employ iron(ii) complexes [Fe(dpbz)]Br2 (dpbz = 1,2-bis(diphenylphosphino)benzene) and FeBr2/Et3N, respectively. [Fe(dpbz)]Br2 was found to be highly effective at converting 2-azido-2,3-dihydro-1H-inden-1-ones to isoquinolones. The reagent combination of FeBr2/Et3N, on the other hand, exhibited a broader catalytic scope, owing to the beneficial effect of Et3N. This latter catalyst system enables 2-azido-2-methyl-1,3-dicarbonyl compounds to be converted to the corresponding enamides under mild conditions in good yields.
Iron-Catalyzed Acyl Migration of Tertiary α-Azidyl Ketones: Synthetic Approach toward Enamides and Isoquinolones
Yang, Tonghao,Fan, Xing,Zhao, Xiaopeng,Yu, Wei
supporting information, p. 1875 - 1879 (2018/04/16)
This paper reports that tertiary α-azidyl phenyl ketones can be transformed into enamides by treatment with FeBr2 at elevated temperature in DMF. The reaction proceeds via 1,2-benzoyl migration from α-carbon to the nitrogen atom, accompanied by expulsion of a nitrogen molecule. This protocol is suitable for the synthesis of N-(cyclopent-1-en-1-yl)benzamides, N-(cyclohex-1-en-1-yl)benzamides, and N-benzoyl-α-methyl enamines and provides a convenient approach toward isoquinolones.
A New, Mild Synthesis of N-Sulfonyl Ketimines via the Palladium-Catalyzed Isomerization of Aziridines
Wolfe, John P.,Ney, Joshua E.
, p. 4607 - 4610 (2007/10/03)
(Matrix presented) A new method for the synthesis of N-tosylketimines via the palladium-catalyzed isomerization of N-tosylaziridines is described. The mild reaction conditions tolerate the presence of a variety of functional groups including ketones, este
Thermolyse von Oxazolin-5-onen, XI. N-Acylimine und Enamide durch Gasphasenpyrolyse von 4-Alkyl-2-oxazoline-5-onen
Jendrzejewski, Stefan,Steglich, Wolfgang
, p. 1337 - 1342 (2007/10/02)
On gas phase thermolysis 4-alkyl-2-oxazolin-5-ones 1 undergo CO elimination to yield N-acylimines 2, which rearrange into more stable enamides 3 if α-hydrogens are present.N-Acylimines (e.g. 2a) may be isolated in cases where the rearrangement is prevented by a quarternary C-atom.The 4,4-dialkylsubstituted oxazolinone 1o yields mixtures of N-acylimine 2o and enamide 3o, the amount of the latter increasing at higher pyrolysis temperatures.
