Search results for "piperidine"

Stereocontrolled Synthesis of Fluorine-Containing Piperidine γ-Amino Acid Derivatives

2018

Diversity-Oriented Stereocontrolled Synthesis of Some Piperidine- and Azepane-Based Fluorine-Containing β-Amino Acid Derivatives

2020

AbstractStructural diversity-oriented synthesis of some azaheterocyclic β-amino acid derivatives has been accomplished by selective functionalization of readily available cyclodienes. The stereocontrolled synthetic concept was based on the oxidative ring cleavage of unsaturated cyclic β-amino acids derived from cycloalkadiene, followed by ring closing with double reductive amination, which furnished some conformationally restricted β-amino acid derivatives with a piperidine or azepane core.

Palladium-Catalyzed C—C Coupling Reactions in the Enantioselective Synthesis of 2,4-Disubstituted 4,5-Dehydropiperidines Using Galactosylamine as a S…

2005

Abstract Stereoselective synthesis of enantiomerically pure 2,4-disubstituted piperidine derivatives, which are considered interesting pharmacophoric structures, was achieved starting with a tandem Mannich–Michael reaction sequence on O -pivaloylated N -galactosyl aldimines. Subsequent conversion of the thus formed 2-substituted dehydropiperidinones into the corresponding enol triflates was carried out by conjugate hydride addition and trapping the enolate with N , N -bis(trifluoromethanesulfonyl)aniline. Their Suzuki–Miyaura coupling with aryl and heteroaryl boronic acids was performed under conditions compatible with the carbohydrate structure, in particular, with the sensitive N -glycosi…

Amino Acid Esters as Chiral Auxiliary Groups in Lewis Acid Catalyzed Reactions of Electron-rich Siloxydienes with Imines

1990

Synthesis of fluorinated piperidine and azepane β-amino acid derivatives

2016

Abstract A convenient and robust stereocontrolled procedure has been developed for the synthesis of novel trifluoromethyl-containing piperidine and azepane β-amino ester stereoisomers. The synthesis started from readily available unsaturated bicyclic β-lactams and was based on oxidative cleavage of the ring C C double bond followed by ring closure of the diformyl intermediates in the presence of 2,2,2-trifluoroethylamine hydrochloride through reductive amination. The synthetic procedure has efficiently been extended towards the synthesis of mono- and difluorinated analogs.

The ionic liquid effect on the Boulton-Katritzky reaction: a comparison between substrates of different structure

2015

The mononuclear rearrangement of heterocycles, also called Boulton–Katritzky reaction, was studied in ionic liquid solution using N-(5-phenyl-1,2,4-oxadiazol-3-yl)-N′-(4-nitrophenyl)-formamidine as substrate. The investigation was carried out using piperidine as basic catalyst and several ionic liquids differing in both cation and anion structure. Kinetic data collected were compared with the ones previously reported using (Z)-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole to have information about the effect due to the different structure of the alkyl chain borne on the substrate. Furthermore, data were analysed on the grounds of polarity, Kamlet–Taft solvent parameters, but taking…

On the Dichotomic Behavior of the Z-2,4-Dinitrophenylhydrazone of 5-Amino-3-benzoyl-1,2,4-oxadiazole with Acids in Toluene and in Dioxane/Water:  Rea…

2004

The mononuclear rearrangement (MRH) of the Z-2,4-dinitrophenylhydrazone (4a) and of the Z-phenylhydrazone (4b) of 5-amino-3-benzoyl-1,2,4-oxadiazole into the relevant triazoles 5a and 5b in toluene has been quantitatively investigated in the presence of trichloroacetic acid (TCA) and of piperidine at 313.1 K. While the behavior in the presence of piperidine recalls the one previously evidenced for some Z-hydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole, the study of the reactivity in the presence of TCA has most interestingly evidenced a general-acid-catalyzed rearrangement for “both” 4a and 4b. Thus, 4a offers the first example of a solvent-dependent dichotomic behavior in MRH processes o…

Arabinosylamine in Asymmetric Syntheses of Chiral Piperidine Alkaloids.

2004

The stereodifferentiating potential of arabinosyl aldimines was utilized in stereoselective syntheses of 2-substituted dehydropiperidinones and their further transformation to 2,6-cis-substituted piperidinones. The absolute configuration was proven by X-ray analysis and by the synthesis of the enantiomerically pure alkaloid (+)-dihydropinidine. The presented method offers the possibility to synthesize piperidine derivatives enantiomeric to those obtained by the application of the corresponding galactosylamine auxiliary.

C−C versus C−N Annulation Reactions of 2-Alkyl-2-oxazolines and 2-Alkyl-2-thiazolines: A Simple Synthesis of Novel 3-Aminoindene, Phthalimidine, Pyrr…

2001

The effect of various aromatic and aliphatic dielectrophiles on the lithium azaenolates of 2-alkyl-2-oxazolines and 2-alkyl-2-thiazolines has been examined. This effect varies greatly, depending on the nature of the dielectrophile used. 3-Aminoindene (3) and 3-alkylidenephthalimidine (4−5) derivatives were formed as a result of the reactions with dielectrophiles derived from ortho-substituted benzonitriles. Similarly, 2-alkylidenepyrrolidine (7) and 2-alkylidenepiperidine (8) derivatives were obtained in high yields from 2-alkyl-2-oxazolines or 2-alkyl-2-thiazolines and aliphatic dielectrophiles derived from ω-haloalkyldiphenylacetonitrile. C−C versus C−N annulation reactions are discussed.

ChemInform Abstract: C-C versus C-N Annulation Reactions of 2-Alkyl-2-oxazolines and 2-Alkyl-2-thiazolines: A Simple Synthesis of Novel 3-Aminoindene…

2010

The effect of various aromatic and aliphatic dielectrophiles on the lithium azaenolates of 2-alkyl-2-oxazolines and 2-alkyl-2-thiazolines has been examined. This effect varies greatly, depending on the nature of the dielectrophile used. 3-Aminoindene (3) and 3-alkylidenephthalimidine (4−5) derivatives were formed as a result of the reactions with dielectrophiles derived from ortho-substituted benzonitriles. Similarly, 2-alkylidenepyrrolidine (7) and 2-alkylidenepiperidine (8) derivatives were obtained in high yields from 2-alkyl-2-oxazolines or 2-alkyl-2-thiazolines and aliphatic dielectrophiles derived from ω-haloalkyldiphenylacetonitrile. C−C versus C−N annulation reactions are discussed.