91640-05-0

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 2430, 1988 DOI: 10.1021/jo00246a008

Upstream product

• 106051-09-6 5-methyl-6-phenyl-4-oxa-5-azaspiro<2.4>heptane 
• 3376-23-6 N-methyl-α-phenylnitrone 
• 653579-35-2 1-[2-(methylamino)-2-phenylethyl]cyclopropanol 
• 3376-23-6 N-(benzylidene)methylamine N-oxide 
• 6142-73-0 methylene cyclopropane 
• 5409-51-8 (E)-5-dimethylamino-1-phenylpent-1-en-3-one hydrochloride 
• 74-89-5 methylamine 

Relevant academic research and scientific papers

A two-step, formal [4 + 2] approach toward piperidin-4-ones via au catalysis

(Chemical Equation Presented) An efficient, formal [4 + 2] synthesis of synthetically valuable piperidin-4-ones from secondary amines in two steps has been achieved via a key gold catalysis without the purification of tertiary amine intermediates. This reaction is selective toward the less-substituted alkyl group and shows moderate to excellent diastereoselectivities. Its synthetic potential in alkaloid synthesis is demonstratedin a highly diastereoselective synthesis of (±)-cermizine C.

Two-step metal-mediated transformation of isoxazolidine-5- spirocyclopropanes into pyridone derivatives

The two-step metal-catalyzed overall transformation of isoxazolidine-5- spirocyclopropanes into the corresponding dihydro- and tetrahydropyridones is described. The first step is the chemoselective reduction of the N-O bond of the isoxazolidine ring prese

Domino Palladium(II)-Mediated Rearrangement-Oxidative Cyclization of β-Aminocyclopropanols

β-Aminocyclopropanols were transformed, in a domino process catalyzed by Pd(II) salts, into the corresponding 2,3-dihydro-1H-pyridin-4-ones. Conversely the use of a Pd(0) derivative, Pd(dba)2, afforded the corresponding tetrahydropyrid-4-ones. The saturated derivatives were also obtained, in better yields, using Pd(II) and Cu(OAc)2 as stoichiometric oxidant.

SYNTHESIS OF SUBSTITUTED 2-PHENYL-4-PIPERIDINONES FROM STYRYL β-DIMETHYLAMINOETHYL KETONES AND THEIR STERIC STRUCTURE

The difficultly obtainable substituted 2-phenyl-4-piperidinones were synthesized by the reaction of styryl β-dimethylaminoethyl ketone hydrochlorides with aqueous solutions of ammonia or alkylamines.It was found using 1H and 13C NMR spectroscopy methods that the cyclization process proceeds with the formation of pure stereoisomers of 4-piperidones with an equatorial disposition of all the substituents in the ring.The temperature for performing the cyclization is dependent on the number and position of the methyl substituents in the molecule of the starting substituted styryl β-dimethylaminoethyl ketones.

REARRANGEMENT OF NITRONE CYCLOADDUCTS TO METHYLENE CYCLOPROPANE. SYNTHESIS OF INDOLIZIDINE AND QUINOLIZIDINE DERIVATIVES.

Isoxazolidines 3, obtained by cycloaddition of nitrones with methylene cyclopropane, undergo thermal rearrangement to piperidin-4-one derivatives.Indolizidine and quinolizidine derivatives are obtained from cyclic nitrones.