Sedum alkaloids XII. Synthesis of the new piperidine alkaloids homosedinone and dihomosedinone

1992 ◽  
Vol 70 (11) ◽  
pp. 2722-2725 ◽  
Author(s):  
Alex Durant ◽  
Claude Hootelé
Keyword(s):  
Nucleophilic Addition ◽  
Piperidine Alkaloids ◽  
Anodic Methoxylation

The new piperidine alkaloids homosedinone 2 and dihomosedinone 3, isolated from Sedumacre, have been synthesized from (−)-norsedamine 7 by application of the sequence: anodic methoxylation – elimination – nucleophilic addition.

Sedum alkaloids. XI. Synthesis of sedinone and sedacrine by application of anodic oxidation

1991 ◽  
Vol 69 (2) ◽  
pp. 211-217 ◽  
Author(s):  
Frank Driessens ◽  
ClaUDE Hootelé
Keyword(s):  
Nucleophilic Substitution ◽  
Key Words ◽  
Anodic Oxidation ◽  
Methoxy Group ◽  
High Yield ◽  
Piperidine Alkaloids ◽  
Piperidine Derivative ◽  
Sedum Acre ◽  
Anodic Methoxylation

α-Methoxycarbamate 12, synthetic precursor of the 2,6-disubstituted alkaloids of Sedum acre, was obtained in high yield from 2-phenacylpiperidine 5; the key step of the synthesis rests on the anodic methoxylation, which allows the functionalization of carbon 6. Nucleophilic substitution of the methoxy group by an acetonyl chain leads, after the required transformations, to sedinone 23. Bromomethoxylation of the enecarbamate 19 followed by dehydrohalogenation and nucleophilic substitution of the methoxy group leads to sedacrine 33. In both cases, the nucleophilic substitution of the methoxy group leads to a cis 2,6-disubstituted piperidine derivative. Key words: synthesis, piperidine alkaloids, anodic methoxylation

Synthesis of β-hydroxypiperidine alkaloids by anodic oxidation of carbamates and hydroboration

1996 ◽  
Vol 74 (12) ◽  
pp. 2444-2453 ◽  
Author(s):  
Mark Plehiers ◽  
Claude Hootelé
Keyword(s):  
Key Words ◽  
Anodic Oxidation ◽  
Nucleophilic Addition ◽  
Piperidine Ring ◽  
Anodic Methoxylation

The β-hydroxypiperidine alkaloids (±)-pseudoconhydrine, (±)-N-methylpseudoconhydrine, (−)-5-hydroxysedamine, and (+)-sedacryptine were synthesized. Successive functionalization of the piperidine ring via anodic methoxylation allowed the regio- and stereoselective introduction of the substituents. The α and α′ substituents were introduced by application of the sequence elimination–nucleophilic addition from 2- or 2,5-substituted 6-methoxycarbamates. Hydroboration – oxidation of enecarbamates, obtained by elimination of methanol from α-methoxycarbamates, allowed the introduction of the β-hydroxy function. Key words: alkaloid, Sedum, N-acyliminium, enecarbamate.

Recent Progress in Chemosensors Using Aldehyde-bearing Fluorophores for the Detection of Specific Analytes and their Bioimaging

2019 ◽  
Vol 26 (21) ◽  
pp. 4003-4028 ◽  
Author(s):  
Fangjun Huo ◽  
Yaqiong Zhang ◽  
Caixia Yin
Keyword(s):  
Biomedical Research ◽  
Nucleophilic Addition ◽  
Recent Progress ◽  
Biological Imaging ◽  
Tissue Imaging ◽  
Fluorescence Probes ◽  
Biological Applications ◽  
Convenient Procedure ◽  
Nucleophilic Mechanism

In recent years, aldehyde-appended fluorescence probes have attracted increasing attention. Fluorescent biological imaging includes many modern applications for cell and tissue imaging in biomedical research. Meanwhile, the nucleophilic mechanism is a very simple and convenient procedure for the preparation of aldehyde-sensing probes. This tutorial review focuses on aldehyde-bearing chemosensors based on nucleophilic addition mechanism with biological applications.

Formation of spiro adduct from N-methyl-N-(2,4,6-trinitrophenyl)glycine anion

1989 ◽  
Vol 54 (2) ◽  
pp. 440-445 ◽  
Author(s):  
Vladimír Macháček ◽  
Alexandr Čegan ◽  
Miloš Sedlák ◽  
Vojeslav Štěrba
Keyword(s):  
Nmr Spectroscopy ◽  
Dimethyl Sulfoxide ◽  
Equilibrium Constant ◽  
Mole Fraction ◽  
Nucleophilic Addition ◽  
Adduct Formation ◽  
First Case ◽  
C Nmr

The intramolecular nucleophilic addition of N-methyl-N-(2,4,6-trinitrophenyl)glycine anion in methanol-dimethyl sulfoxide mixtures produces spiro[(3-methyl-5-oxazolidinone)-2,1'-(2',4',6'-trinitrobenzenide)]. The spiro adduct has been identified by means of 1H and 13C NMR spectroscopy. This is the first case when the formation of a Meisenheimer adduct with carboxylate ion is observed. Logarithm of the equilibrium constant of adduct formation increases linearly with the mole fraction of dimethyl sulfoxide in its mixture with methanol.

Regioselective Functionalization of N-Fused Heteroaromatics via FeCl3-Catalyzed Nucleophilic Addition to Activated N-Heterocycles

Synthesis ◽  
2020 ◽  
Author(s):  
Ikyon Kim ◽  
Sung June Kim ◽  
Sunhee Lee
Keyword(s):  
Aromatic Compounds ◽  
Nucleophilic Addition ◽  
Chemical Space ◽  
Wide Range ◽  
Regioselective Functionalization

AbstractBroadening of nitrogen-fused heteroaromatic chemical space such as indolizine and pyrrolo[1,2-a]pyrazine was achieved via FeCl­3-catalyzed nucleophilic addition of these N-fused aromatic compounds to a wide range of azolinium systems generated in situ, leading to novel N-fused heteroaromatic scaffolds with dearomatized N-heterocyclic substituents regioselectively. Nucleophilic addition of indolizines and pyrrolo[1,2-a]pyrazines mainly occurred at the C1 position of the isoquinoliniums and at the C4 site of the quinoliniums.

Layer by layer assembled functionalized graphene oxide-based polymer brushes for superlubricity on steel-steel tribocontact

Soft Matter ◽  
2021 ◽  
Author(s):  
Suprakash Samanta ◽  
Rashmi Ranjan Sahoo
Keyword(s):  
Graphene Oxide ◽  
Nucleophilic Addition ◽  
Polymer Brushes ◽  
Addition Reaction ◽  
Layer By Layer ◽  
Functionalized Graphene ◽  
Covalent Functionalization ◽  
Functionalized Graphene Oxide ◽  
Nucleophilic Addition Reaction ◽  
Branched Polyethylenimine

Present study demonstrates a simple and multistep approach for the preparation of covalent functionalization of chemically prepared graphene oxide (GO) by branched polyethylenimine (PEI) through nucleophilic addition reaction to prepare...

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