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Beilstein Journal of Organic Chemistry

Satoru Mori, Norio Shibata
Phthalocyanines and subphthalocyanines are attracting attention as functional dyes that are applicable to organic solar cells, photodynamic therapy, organic electronic devices, and other applications. However, phthalocyanines are generally difficult to handle due to their strong ability to aggregate, so this property must be controlled for further applications of phthalocyanines. On the other hand, trifluoroethoxy-substituted phthalocyanines are known to suppress aggregation due to repulsion of the trifluoroethoxy group...
2017: Beilstein Journal of Organic Chemistry
Henning Weiss, Jeannine Reichel, Helmar Görls, Kilian Rolf Anton Schneider, Mathias Micheel, Michael Pröhl, Michael Gottschaldt, Benjamin Dietzek, Wolfgang Weigand
Eight difluoroboron complexes of curcumin derivatives carrying alkyne groups containing substituents have been synthesized following an optimised reaction pathway. The complexes were received in yields up to 98% and high purities. Their properties as fluorescent dyes have been investigated. Furthermore, a strategy for the hydrolysis of the BF2 group has been established using aqueous methanol and sodium hydroxide or triethylamine.
2017: Beilstein Journal of Organic Chemistry
Magdalena Ceborska, Magdalena Zimnicka, Aneta Aniela Kowalska, Kajetan Dąbrowa, Barbara Repeć
The complexation of the antifolate pemetrexed (PTX) with native cyclodextrins was studied. This process, along with the findings gathered for the structurally related folic acid was treated as a model for exploiting host-guest interactions of this class of guest molecules in the gas phase, in solution and in the solid state. Mass spectrometry was employed for the investigation of the architecture and relative gas-phase stabilities of these supramolecular complexes. The mode of complexation was further tracked by 1D and 2D NMR proving the formation of the exclusion-type complex with α-CD and pseudorotaxane inclusion-type complexes with β-, and γ-CDs...
2017: Beilstein Journal of Organic Chemistry
Grzegorz Mlostoń, Heinz Heimgartner
The scope of applications of dialkyl dicyanofumarates and maleates as highly functionalized electron-deficient dipolarophiles, dienophiles and Michael acceptors is summarized. The importance for the studies on reaction mechanisms of cycloadditions is demonstrated. Multistep reactions with 1,2-diamines and β-aminoalcohols leading to diverse five- and six-membered heterocycles are discussed. Applications of dialkyl dicyanofumarates as oxidizing agents in the syntheses of disulfides and diselenides are described...
2017: Beilstein Journal of Organic Chemistry
Yaroslav Dmitrievich Boyko, Valentin Sergeevich Dorokhov, Alexey Yu Sukhorukov, Sema Leibovich Ioffe
Despite of their chemical instability and high reactivity, conjugated nitrosoalkenes are useful intermediates in target-oriented organic synthesis. The present review deals with carbon-carbon bond forming reactions involving Michael addition to α-nitrosoalkenes with a particular focus on recent developments in this methodology and its use in total synthesis.
2017: Beilstein Journal of Organic Chemistry
Charlotte M Sevrain, Mathieu Berchel, Hélène Couthon, Paul-Alain Jaffrès
The phosphonic acid functional group, which is characterized by a phosphorus atom bonded to three oxygen atoms (two hydroxy groups and one P=O double bond) and one carbon atom, is employed for many applications due to its structural analogy with the phosphate moiety or to its coordination or supramolecular properties. Phosphonic acids were used for their bioactive properties (drug, pro-drug), for bone targeting, for the design of supramolecular or hybrid materials, for the functionalization of surfaces, for analytical purposes, for medical imaging or as phosphoantigen...
2017: Beilstein Journal of Organic Chemistry
Alexey Yu Dubovtsev, Maksim V Dmitriev, Аndrey N Maslivets, Michael Rubin
The condensation of 5-alkoxycarbonyl-1H-pyrrolediones with cyclic ketazinones was systematically investigated. It was discovered that the regioselectivity of this reaction can be easily swapped between two alternative directions affording derivatives of partially hydrogenated indole or benzofurane. The control of this regioselectivity is efficiently governed by steric effects at the hydrazone moiety of the ketazinone reagent.
2017: Beilstein Journal of Organic Chemistry
Nicolas Pétry, Hafid Benakki, Eric Clot, Pascal Retailleau, Farhate Guenoun, Fatima Asserar, Chakib Sekkat, Thomas-Xavier Métro, Jean Martinez, Frédéric Lamaty
Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline-proline dipeptides under solvent-free conditions. A deprotection-cyclization sequence yielded the corresponding diketopiperazines that were obtained with a high stereoselectivity which could be explained by DFT calculations. Using this method, an enantiopure disubstituted Pro-Pro diketopiperazine was synthesized in 4 steps, making 5 new bonds using a ball mill...
2017: Beilstein Journal of Organic Chemistry
Patrick A Julien, Ivani Malvestiti, Tomislav Friščić
We provide the first in situ and real-time study of the effect of milling frequency on the course of a mechanochemical organic reaction conducted using a vibratory shaker (mixer) ball mill. The use of in situ Raman spectroscopy for real-time monitoring of the mechanochemical synthesis of a 2,3-diphenylquinoxaline derivative revealed a pronounced dependence of chemical reactivity on small variations in milling frequency. In particular, in situ measurements revealed the establishment of two different regimes of reaction kinetics at different frequencies, providing tentative insight into processes of mechanical activation in organic mechanochemical synthesis...
2017: Beilstein Journal of Organic Chemistry
Gerhard Wenz
No abstract text is available yet for this article.
2017: Beilstein Journal of Organic Chemistry
Shital Kumar Chattopadhyay, Suman Sil, Jyoti Prasad Mukherjee
A new synthesis of the important amino acid 2-aminosuberic acid from aspartic acid is reported. The methodology involves the alternate preparation of (S)-2-aminohept-6-enoate ester as a building block and its diversification through a cross-metathesis reaction to prepare the title compounds. The utility of the protocol is demonstrated through the preparation of three suberic acid derivatives of relevance to the design and the synthesis of peptides of biological relevance.
2017: Beilstein Journal of Organic Chemistry
Łukasz Szyszka, Anna Osuch-Kwiatkowska, Mykhaylo A Potopnyk, Sławomir Jarosz
The C12-aminoalditol H2NCH2-(CHOBn)10-CH2OH was prepared from two simple monosaccharide building blocks. The synthesis was realized by a regioselective introduction of the azide group and subsequent protection-deprotection transformations. The chemical reactivity of the aminoalditol was tested in the reductive amination reaction with a selectively protected sucrose monoaldehyde.
2017: Beilstein Journal of Organic Chemistry
Joana M Pais, Maria João Barroca, Maria Paula M Marques, Filipe A Almeida Paz, Susana S Braga
Fisetin is a natural antioxidant with a wide range of nutraceutical properties, including antidiabetic, neuroprotecting, and suppression or prevention of tumors. The present work describes the preparation of a water-soluble, solid inclusion compound of fisetin with gamma-cyclodextrin (γ-CD), a cyclic oligosaccharide approved for human consumption. A detailed physicochemical analysis of the product is carried out using elemental analysis, powder X-ray diffraction (PXRD), Raman, infrared and (13)C{(1)H} CP-MAS NMR spectroscopies, and thermal analysis (TGA) to verify fisetin inclusion and to present a hypothetical structural arrangement for the host-guest units...
2017: Beilstein Journal of Organic Chemistry
Tao Wang, Yan-Chao Zhao, Li-Min Zhang, Yi Cui, Chang-Shan Zhang, Bao-Hang Han
We successfully employed bisphenol A and several different formyl-containing monomers as useful building blocks to construct a series of hydroxy-group-containing porous organic polymers in a sealed tube at high temperature. Fourier transform infrared and solid-state (13)C CP/MAS NMR spectroscopy are utilized to characterize the possible structure of the obtained polymers. The highest Brunauer-Emmet-Teller specific surface area of the phenolic-resin porous organic polymers (PPOPs) is estimated to be 920 m(2) g(-1)...
2017: Beilstein Journal of Organic Chemistry
Mario Pérez-Venegas, Gloria Reyes-Rangel, Adrián Neri, Jaime Escalante, Eusebio Juaristi
[This corrects the article DOI: 10.3762/bjoc.13.167.].
2017: Beilstein Journal of Organic Chemistry
James R Vyvyan, Courtney A Engles, Scott L Bray, Erik D Wold, Christopher L Porter, Mikhail O Konev
Several Hiyama cross-coupling reactions of oxasilacycloalkenes and aryl iodides are described that produce trisubstituted Z-styrenes in moderate to excellent yields. Both electron-rich and electron-poor aryl iodides are tolerated in the cross-coupling reaction. The oxasilacycloalkene coupling partners were prepared by ruthenium-catalyzed intramolecular anti-hydrosilylation of alkynols. One of the cross-coupling products was converted to a 1-benzoxocane, albeit in low yield, using an intramolecular Buchwald-Hartwig etherification...
2017: Beilstein Journal of Organic Chemistry
Layal Hariss, Kamal Bou Hadir, Mirvat El-Masri, Thierry Roisnel, René Grée, Ali Hachem
Using an aerobic oxidative coupling, different new imidazo[1,2-a]-N-heterocycles with gem-difluroroalkyl side chains have been prepared in fair yields by the reaction of gem-difluoroenones with aminopyridines, -pyrimidines and -pyridazines. Condensed heterocycles of this type play an important role as key core structures of various bioactive compounds. Further, starting with a chloroimidazopyridazine derivative, Pd-catalyzed coupling reactions as well as nucleophilic substitutions have been performed successfully in order to increase the molecular diversity...
2017: Beilstein Journal of Organic Chemistry
Weizhun Yang, Bo Yang, Sherif Ramadan, Xuefei Huang
Most glycosylation reactions are performed by mixing the glycosyl donor and acceptor together followed by the addition of a promoter. While many oligosaccharides have been synthesized successfully using this premixed strategy, extensive protective group manipulation and aglycon adjustment often need to be performed on oligosaccharide intermediates, which lower the overall synthetic efficiency. Preactivation-based glycosylation refers to strategies where the glycosyl donor is activated by a promoter in the absence of an acceptor...
2017: Beilstein Journal of Organic Chemistry
Neha Rana, Manish Kumar, Vinod Khatri, Jyotirmoy Maity, Ashok K Prasad
Conversion of D-glucose to 4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-ribofuranose, which is a key precursor for the synthesis of different types of bicyclic/spiro nucleosides, led to the formation of an inseparable 1:1 mixture of the desired product and 4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-xylofuranose. A convenient environment friendly Novozyme(®)-435 catalyzed selective acetylation methodology has been developed for the separation of an epimeric mixture of ribo- and xylotrihydroxyfuranosides in quantitative yields...
2017: Beilstein Journal of Organic Chemistry
Agota A Gečiauskaitė, Felipe García
Over the past decade, mechanochemistry has emerged as a powerful methodology in the search for sustainable alternatives to conventional solvent-based synthetic routes. Mechanochemistry has already been successfully applied to the synthesis of active pharmaceutical ingredients (APIs), organic compounds, metal oxides, coordination compounds and organometallic complexes. In the main group arena, examples of synthetic mechanochemical methodologies, whilst still relatively sporadic, are on the rise. This short review provides an overview of recent advances and achievements in this area that further validate mechanochemistry as a credible alternative to solution-based methods for the synthesis of main group compounds and frameworks...
2017: Beilstein Journal of Organic Chemistry
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