Tocopherols by Hydride Reduction of Dialkylamino Derivatives

Netscher, Thomas; Mazzini, Francesco; Jestin, Roselyne

doi:10.1002/ejoc.200600874

Cited by 25 publications

(25 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(250 3 4.6 mm, particle size 5 lm, eluent 0.5% EtOH in n-hexane, flow 1.0 ml/min, k 5 296 nm). (2R,4 0 R,8 0 R)-d-tocopherol (4) was available from previous work, 26 chemical purity 98.6% (GC, acetate derivative), optical purity >99% by chiral HPLC analysis of the methyl ether derivative 27 on a Chiralcel OD column from Daicel Chem. Ind.…”

Section: Methodsmentioning

confidence: 99%

Circular dichroism of tocopherols versus tocotrienols

Mazzini

Bari

Netscher³

et al. 2008

Chirality

Self Cite

View full text Add to dashboard Cite

Vitamin E is an essential nutrient of still increasing economic importance. Vitamin E derivatives include many nonracemic chiral compounds whose chirooptical characterization is scarcely described in the literature. We report the CD spectra of delta-tocopherol and its unsaturated analog delta-tocotrienol. TDDFT calculations demonstrate that the weak CD of delta-tocopherol is determined by the helicity of dihydropyrane ring. In addition, the moderate CD of delta-tocotrienol is due to the exciton interaction between the aromatic ring and the closest alkene group. Direct exciton-coupled CD calculations on structures generated by two different conformational sampling approaches reveal that, although such exciton coupling is expected to be weak, it is sufficient to explain the spectral differences between tocopherol and tocotrienol.

show abstract

Section: Methodsmentioning

confidence: 99%

Circular dichroism of tocopherols versus tocotrienols

Mazzini

Bari

Netscher³

et al. 2008

Chirality

Self Cite

View full text Add to dashboard Cite

show abstract

“…48,49 When formaldehyde and morpholine were reacted at 25 °C in CD 3 CN, both hemiaminal (HA) and bisaminal (BA) were formed in 56 and 44% yields, respectively, in the reaction mixture as shown by the 1 H NMR analysis ( Figure 1a and Table 1). The experiment was carried out without any drying process for the reagents.…”

Section: Resultsmentioning

confidence: 96%

Mechanistic studies on the metal-free decarboxylative coupling reaction for synthesis of propargylamines by NMR

Lee¹,

Park²,

Kim³

et al. 2016

Arkivoc

View full text Add to dashboard Cite

Metal-free decarboxylative coupling reaction of phenylpropiolic acid, paraformaldehyde, and morpholine was monitored by NMR spectroscopy ( 1 H, 13 C NMR, NOE, DOSY, COSY HMBC, and HSQC). Hemiaminal and bisaminal were obtained from the reaction with paraformaldehyde and morpholine. The resulting hemiaminal was more reactive than the corresponding bisaminal in the reaction with phenylpropiolic acid. The decarboxylative coupling with hemiaminal and phenylpropiolic acid may be the major pathway, producing the desired phenylpropargylamine.

show abstract

“…[2] Formation of 3a-c was expected to occur by a sulphonation process at C-5, in the enole form [III] giving the sulfonic acid intermediate [IV] (not isolated). Thus, by elimination of sulfonic acid, [24][25][26] compounds 3 were formed (Scheme 3, pathway i).…”

Section: Resultsmentioning

confidence: 99%

Advancements in synthesis of pharmacologically active imidazolidin‐4‐ones and stereochemistry of their Reactions with some Reagents

Saied

Abdelwahab

Hashem

et al. 2020

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

1‐Aryl, 1,3‐diaryl‐ and 5‐(2‐oxo‐2‐arylethyl)‐2‐thioxo‐imidazolidin‐4‐ones 2 were prepared as before, nevertheless, equivalent amounts of potassium hydroxide were added to the reaction conditions. This change, dramatically, reduced the reaction time and highly increased the yield of some derivatives. Treatment of 2 with sulfuric acid converted them into their analogous (E)/(E,Z)‐5‐(2‐oxo‐2‐arylethylidene) derivatives 3. Reactions of 2 and/or 3 with chromium trioxide affected their conversion into the corresponding 2,4‐diones 4 and 5, respectively. Treatment of 2 and/or 3 with ethyl bromoacetate affected conversion of the former into their respective 2,4‐diones 4, whereas it gave the respective 2‐alkylthio derivatives of the latter. Reactions of 2b with aromatic aldehydes gave mixtures of spiro‐1H‐ and 2H‐pyrrole diastereomers. Structures of the new products were evidenced by infrared, EI‐MS, 1H‐ and 13C‐NMR spectroscopic measurements. Many of the selected compounds showed good antimicrobial activity.

show abstract

Tocopherols by Hydride Reduction of Dialkylamino Derivatives

Cited by 25 publications

References 20 publications

Circular dichroism of tocopherols versus tocotrienols

Circular dichroism of tocopherols versus tocotrienols

Mechanistic studies on the metal-free decarboxylative coupling reaction for synthesis of propargylamines by NMR

Advancements in synthesis of pharmacologically active imidazolidin‐4‐ones and stereochemistry of their Reactions with some Reagents

Contact Info

Product

Resources

About