62183-16-8Relevant academic research and scientific papers
Geometry Driven Intramolecular Oxidative Cyclization of Enamides: An Umpolung Annulation of Primary Benzamides with Acrylates for the Synthesis of 3-Methyleneisoindolin-1-ones
Laha, Joydev K.,Kaur Hunjan, Mandeep,Bhimpuria, Rohan A.,Kathuria, Deepika,Bharatam, Prasad V.
, p. 7346 - 7352 (2017)
A palladium-catalyzed tandem oxidative annulation of primary benzamides with acrylates via intermolecular N-alkenylation followed by intramolecular C-alkenylation yielded a stereoselective synthesis of (E)-3-methyleneisoindolin-1-ones. The study unveils, for the first time, that only E-enamides could undergo intramolecular oxidative cyclization under the optimized conditions to give isoindolinones. The current strategy represents an umpolung strategy when compared to the literature approaches that use benzamides.
Metal-Free Stereoselective Synthesis of (E)- And (Z)-N-Monosubstituted β-Aminoacrylates via Condensation Reactions of Carbamates
Dion, Amélie,Pollack, Scott R.
supporting information, p. 11748 - 11762 (2021/09/07)
N-monosubstituted β-aminoacrylates are building blocks, which have been used in the preparation of amino acids and pharmaceuticals. Two efficient, stereoselective methods of preparation, via acid- or base-promoted condensation reactions of carbamates, are described. The base-promoted reaction is E-selective, while acid catalysis can, through the choice of solvent, selectively form E or Z. The acid-catalyzed E-selective process proceeds through a crystallization obviating the need for chromatographic purification.
α,β-Dehydrogenation of esters with free O–H and N–H functionalities via allyl-palladium catalysis
Szewczyk, Suzanne M.,Zhao, Yizhou,Sakai, Holt A.,Dube, Pascal,Newhouse, Timothy R.
, p. 3293 - 3300 (2018/03/21)
A direct and selective method for the α,β-dehydrogenation of esters using palladium catalysis in the presence of free O–H and N–H functionalities is reported herein. Allyl-palladium catalysis allows for preservation of readily oxidizable functionalities s
Synthesis of substituted oxazoles from enamides
Panda, Niranjan,Mothkuri, Raghavender
, p. 5727 - 5735 (2015/01/16)
Annulation of enamides into 2,5- and 2,4,5-substituted oxazoles by NBS/Me2S in the presence of mild base has been achieved. The reaction conditions are simple and tolerant to a wide variety of substituents including both electron-donating and withdrawing groups to produce oxazoles in one-pot without further purification of the intermediate.
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.
