Photochemically Induced Solid State Dimerisation of Resveratrol Analogues: A Greener Synthetic Process

2020 ◽  
Vol 73 (12) ◽  
pp. 1260
Author(s):  
Basil Danylec ◽  
Eva M. Campi ◽  
Craig M. Forsyth ◽  
Reinhard I. Boysen ◽  
Milton T. W. Hearn
Keyword(s):  
Solid State ◽  
Parent Compound ◽  
Phenyl Group ◽  
Close Packing ◽  
High Yield ◽  
Synthetic Process ◽  
Cyclobutane Dimer ◽  
Cyclobutane Dimers ◽  
Resveratrol Analogues ◽  
Cyclobutane Derivative

The photochemical dimerisation of resveratrol analogues in the solid state to generate chiral phenyl substituted cyclobutanes is described. NMR spectroscopic and X-ray crystallographic methods have confirmed that the dimerisation leads to the head to tail orientation of the phenyl group substituents in the cyclobutane derivative. Interestingly, the parent compound, resveratrol, in the solid state, did not form a cyclobutane dimer, but the O-acetyl analogues gave the corresponding cyclobutane dimers in high yield, suggesting that the close packing of molecules together with the electron density through the conjugated double bond of the resveratrol structure are important determinants for photodimerisation to occur in the solid state.

scholarly journals Multistep batch-flow hybrid synthesis of a terbinafine precursor

2021 ◽  
Author(s):  
Tamás Hergert ◽  
Béla Mátravölgyi ◽  
Róbert Örkényi ◽  
János Éles ◽  
Ferenc Faigl
Keyword(s):  
Methyl Ether ◽  
Lithium Salt ◽  
Scale Up ◽  
Hybrid Process ◽  
High Yield ◽  
Grignard Reaction ◽  
Efficient Synthesis ◽  
Synthetic Process ◽  
Synthesis Route ◽  
Selective Addition

AbstractA three-step batch-flow hybrid process has been developed for an expeditious synthesis of the enynol key intermediate of antifungal terbinafine. This procedure involves consecutive organometallic steps without the necessity of any in-line purification: after a metalation by n-butyllithium, a selective addition of the lithium salt was elaborated followed by a Grignard reaction resulting in a high yield of 6,6-dimethylhept-1-en-4-yn-3-ol. Moreover, as an alternative to tetrahydrofuran, cyclopentyl methyl ether was used as solvent implementing a safe, sustainable, yet selective synthetic process. Even on a laboratory-scale, the optimized batch-flow hybrid process had a theoretical throughput of 41 g/h. Furthermore, the newly developed process provides an efficient synthesis route to the key-intermediate, while making acrolein obsolete, minimizing side-products, and enabling safe and convenient scale-up.

A rhodamine-naphthalimide-benzamide trichromophoric system with solid-state and multiple solvent dependent aggregate emissive properties

2021 ◽  
Author(s):  
Hemant Sharma ◽  
Kyle Hearn ◽  
Anna Ranieri ◽  
Chiara Caporale ◽  
Massimiliano Massi ◽  
...  
Keyword(s):  
Solid State ◽  
High Yield ◽  
Pure Dmso

A multiresponsive rhodamine-naphthalimide-benzamide conjugate was synthesised in high yield in three steps. The trichromophoric system formed emissive aggregates in pure DMSO that were remarkably sensitive to traces of water (<1...

scholarly journals Reactive Structures in Wood and High-yield Pulps. IV. Daylight-induced Oxidation of Stilbene Structures in the Solid State.

1994 ◽  
Vol 48 ◽  
pp. 490-497 ◽  
Author(s):  
Liming Zhang ◽  
Göran Gellerstedt ◽  
Tai-Cheng Sheng ◽  
Ragnar Larsson ◽  
G. Liptay ◽  
...  
Keyword(s):  
Solid State ◽  
High Yield

scholarly journals Kinetic Study of Glucosamine Production Using Aspergillus sydowii BCRC 31742 under Solid-State Fermentation

Molecules ◽  
2020 ◽  
Vol 25 (20) ◽  
pp. 4832
Author(s):  
Jia Wei Peng ◽  
Ho Shing Wu
Keyword(s):  
Solid State ◽  
Moisture Content ◽  
Solid State Fermentation ◽  
Low Cost ◽  
High Yield ◽  
Aspergillus Sydowii ◽  
Fermentation Conditions ◽  
High Productivity ◽  
State Culture ◽  
Solid State Culture

In the present study, we aimed to obtain a high yield and productivity for glucosamine using a low-cost solid-state culture with Aspergillus sydowii BCRC 31742. The fermentation conditions, such as inoculum biomass, moisture content, and supplemental volume and mineral salt, were chosen to achieve high productivity of glucosamine (GlcN). When the initial supplemental volume used was 3 mL/g substrate, the yield and productivity of GlcN were 48.7 mg/gds and 0.69 mg/gds·h, respectively. This result will be helpful for the industrialization of the process.

High-Yield Hypocrellin A Production in Solid-State Fermentation by Shiraia sp. SUPER-H168

2009 ◽  
Vol 160 (8) ◽  
pp. 2275-2286 ◽  
Author(s):  
Yujie Cai ◽  
Xiaohui Liang ◽  
Xiangru Liao ◽  
Yanrui Ding ◽  
Jun Sun ◽  
...  
Keyword(s):  
Solid State ◽  
Solid State Fermentation ◽  
High Yield ◽  
Hypocrellin A

Synthesis of Casein Related Peptides and Phosphopeptides. XIV. Solid Phase Synthesis of Glu-Ser(P)-Leu Through the Use of Protected Boc-Ser(PO3R2)-OH Derivatives

1991 ◽  
Vol 44 (6) ◽  
pp. 771 ◽  
Author(s):  
JW Perich ◽  
RM Valerio ◽  
PF Alewood ◽  
RB Johns
Keyword(s):  
High Pressure ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Phenyl Group ◽  
High Yield ◽  
Palladium Acetate ◽  
Phase Method ◽  
Phenyl Phosphate ◽  
One Step ◽  
The One

A solid phase method is described for the synthesis of O- phosphoseryl-containing peptides by the use of polystyrene resin (Merrifield) as the peptide support and protected Boc-Ser(PO3R2)-OH derivatives for the incorporation of the phosphorylated seryl residue. The viability of this solid phase approach was demonstrated by the synthesis of HBr.H-Glu-Ser (PO3Et2)-Leu-OH in high yield by the use of Bo -Ser(PO3Et2)-OH in peptide synthesis and subsequent use of HBr/CF3CO2H for cleavage of the Ser(PO3Et2)-containing tripeptide from the resin support. Similarly, the dipeptide, CF3CO2H.H-Ser(P)- Leu -OH, was prepared in high yield by using Boc -Ser(PO3But2)-OH in peptide synthesis followed by the one-step deprotection of the Ser(PO3But2)- dipeptide resin by treatment with HBr/CF3CO2H (90 min). Alternatively, the O-phosphoseryl tripeptide , CF3CO2H.H-Glu-Ser(P)- Leu -OH was prepared by using either Ppoc -Ser(PO3Bzl2)-OH or Boc-Ser(PO3Ph2)-OH in peptide synthesis. The one-step deprotection of the Ser(PO3Bzl2)-containing tripeptide and cleavage of the peptide from the resin support was effected by high-pressure hydrogenolysis (palladium acetate). In the case of phenyl phosphate protection, the Ser(PO3Ph2)-containing peptide was cleaved from the resin support by high-pressure hydrogenolysis (palladium acetate) followed by cleavage of the phenyl phosphate groups by platinum-mediated hydrogenolysis (1.0 equiv. PtO2/phenyl group) in 50% CF3CO2H/AcOH.

Quench-resistant and stable nanocarbon dot/sheet emitters with tunable solid-state fluorescence via aggregation-induced color switching

Nanoscale ◽  
2019 ◽  
Vol 11 (5) ◽  
pp. 2131-2137 ◽  
Author(s):  
Qing Chang ◽  
Yamei Ding ◽  
Shuai Cheng ◽  
Wei Shen ◽  
Zhe Zhou ◽  
...  
Keyword(s):  
Solid State ◽  
High Yield ◽  
Film Forming ◽  
Color Tunable ◽  
Solid State Fluorescence ◽  
Color Switching

Color tunable and stable nanocarbon dot/sheet emitters have been prepared with the merits of high yield, solid state photoluminescence and film-forming ability.

Ruthenium(II)-nitrosyl polypyridinyl Complexes: from NO/ON Isomerization to NO delivery

2015 ◽  
Vol 1767 ◽  
pp. 65-74
Author(s):  
Pascal G. Lacroix ◽  
Isabelle Malfant
Keyword(s):  
Solid State ◽  
Photon Absorption ◽  
High Yield ◽  
Absorption Process ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Ruthenium Nitrosyl ◽  
Nlo Response ◽  
No Release ◽  
Computational Strategy

ABSTRACTRuthenium-nitrosyl (RuII(NO)) complexes are stable in the dark, but exhibit a unique photoreactivity which can lead either to a solid state isomerization from RuII(NO) to RuII(ON), or to a nitric oxide (NO·) release in solution. From our recent discovery of a high yield of isomerization (> 92%) in [RuII(py)4Cl(NO)](PF6)2, we have developed a computational strategy aimed at designing switchable nonlinear optical (NLO) material with high contrast (large difference in the on / off NLO response) in the solid state. Our synthetic targets are terpyridine based RuII chromophores in which various substituents can be introduced to adjust the NLO response which, at best, should be vanishing in the off state. Alternatively, these complexes can undergo a photo-induced NO· release in solution, a possibility which becomes increasingly appealing in relation to the discovery of the numerous biological roles of NO·, in the context of the emergence of the photodynamic therapy. A promising fluorene-terpyridine RuII(NO) complex was investigated, which could find an additional interest in relation to its capability for releasing NO· by a two-photon absorption process.

The relative stabilities of PhE(NH-t-Bu)2 and PhE(μ-N-t-Bu)2EPh (E = As, Sb, and Bi): X-ray structures of {Li2[PhAs(N-t-Bu)2]}2 and PhE(μ-N-t-Bu)2EPh (E = Sb, Bi)

2003 ◽  
Vol 81 (2) ◽  
pp. 169-174 ◽  
Author(s):  
Glen G Briand ◽  
Tristram Chivers ◽  
Masood Parvez
Keyword(s):  
Solid State ◽  
Nmr Spectra ◽  
Phenyl Group ◽  
Synthetic Approach ◽  
Relative Stabilities ◽  
X Ray ◽  
X Ray Crystallography ◽  
In Trans ◽  
C Nmr

The reaction of PhECl2 with 2 equiv of LiHN-t-Bu has been studied for the series E = As, Sb, and Bi to determine the effect of the phenyl group on subsequent amine condensation processes. For PhAsCl2, the metathesis product PhAs(NH-t-Bu)2 4 was obtained as a colourless oil. Similar reactions involving PhECl2, where E = Sb or Bi, yielded the cyclodipnict(III)azanes PhE(μ-N-t-Bu)2EPh 5 (E = Sb) and 6 (E = Bi), respectively. Treatment of 4 with 2 equiv of n-BuLi produced the dilithium salt Li2[PhAs(N-t-Bu)2] 7a. Products 4, 5, 6, and 7a were characterized by 1H, 7Li (7a), and 13C NMR spectra, while 5, 6, and 7a were also structurally characterized by X-ray crystallography. Compound 7a is dimeric in the solid state via intermolecular Li···N and η6-Li···Ph interactions. The cyclodipnict(III)azanes 5 and 6 have similar structures, with the exocyclic phenyl groups in trans positions relative to the E2N2 ring. This synthetic approach provides a new route to the four-membered rings RE(μ-N-t-Bu)2ER (E = Sb, Bi) and the first example of a bis(organyl)cyclodibism(III)azane.Key words: arsenic, antimony, bismuth, amides, imides.

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