Synthesis and biological evaluation of isatin oxime ether-tethered aryl 1H-1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis

A series of fifteen novel isatin oxime ether-tethered aryl 1H-1,2,3-triazole hybrids 5a-o were designed and synthesized by employing Cu(I) catalyzed azide-alkyne [3+2] cycloaddition (CuAAC) between isatin oxime O-propargyl ether and...

The Formation of Benzoxacin-3-ones via Intramolecular Nicholas Reactions and Synthesis of 8- Membered Heliannuols

The γ- carbonyl cations generated from propargyl ether-(Co2CO)6 complexes undergo intramolecular Nicholas reactions to give dehydrobenzoxacin-3-one-Co2(CO)6 complexes in good yields. Reductive decomplexation and subsequent manipulation allows the synthesis of (±)-heliannuol...

Reaction of Lithiated Propargyl Ethers with Carbonyl Compounds – A Regioselective Route to Furan Derivatives

The deprotonation of 3-aryl-substituted alkyl propargyl ethers with n-butyllithium provides an ambident anion that reacts with carbonyl compounds to provide mixtures of γ-substituted products with alkoxyallene substructure and of α-substituted propargyl ethers. The ratio of the two product types strongly depends on the solvent: in diethyl ether the γ-substituted products predominate whereas the more polar tetrahydrofuran favors the α-adducts. The primary addition products undergo 5-endo-trig or 5-endo-dig cyclizations under various reaction conditions to afford isomeric furan derivatives. The highest selectivity in favor of α-substituted products was achieved by employing a MOM-protected propargyl ether. During the protonation step no evidence for a proton shift leading to an isomeric allenyl anion was found. A brief mechanistic discussion tries to rationalize the observed regio­selectivities.

Preparation and properties of propargyl ether-terminated poly(imide siloxane)s and their composites

The novel propargyl ether-terminated oligo(imide siloxane)s (PTISs) based on 2,2’-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA), aminopropyl-terminated polydimethylsiloxane (APPS), 4,4’-diaminodiphenylmethane (MDA) and p-aminophenyl propargyl ether (APPE) were synthesized. The chemical structures of PTISs were characterized by proton nuclear magnetic resonance (1H NMR) and Fourier transform infrared spectroscopy (FTIR). The PTISs exhibited excellent solubility in organic solvent and had broad processing window. The T300 carbon fabric was used to reinforce the PTIS matrices and prepare the composites (T300CF/PTISs). The thermal stability of the cured PTISs was analyzed by thermogravimetric analysis (TGA). The dynamic thermal mechanical properties of the composites were measured by dynamic thermomechanical analysis (DMA). The results show that the temperature at 5% weight loss (Td5) and residual yield at 800°C (Yr800°C) of the cured PTISs in N2 increase with incorporation of the aromatic diamine, whereas the Yr800°C of the cured PTISs in air decreases with introduction of the aromatic diamine. The elasticity of the composite increases with incorporation of the aromatic diamine, and the peak temperature of loss factor for the composites are higher than 300°C. The flexural strength, tensile strength and interlaminar layer shear strength (ILSS) of the T300CF/PTIS composite display the values of 439 MPa, 427 MPa and 32 MPa at room temperature, respectively. The retention of the flexural strength and ILSS for the T300CF/PTIS composite are above 80% at 250°C.

Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction

Dicobalt hexacarbonyl nucleoside complexes of propargyl ether or esters of 5-substituted uridines react with diverse C-nucleophiles. Synthetic outcomes confirmed that the Nicholas reaction can be carried out in a nucleoside presence, leading to a divergent synthesis of novel metallo-nucleosides enriched with alkene, arene, arylketo, and heterocyclic functions, in the deoxy and ribo series.

Synthesis of One New Sugar Imine Molecule

In this research, the molecule Nand#39;-((E)-5-methoxy-2-((1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4,5-dihydro-1H-1,2,3-triazol-4-yl)methoxy) benzylidene)-4-methyl-1,2,3-thiadiazole-5-carbohydrazide were synthesized and characterized by several conventional analysis methods. Its physical properties and thermal stability was studied. The synthesis was conducted based on D-glucose using concept of click chemistry reaction mechanism. Some of the reaction was conducted using microwave irradiation. The synthesis steps initiated by adding propargyl bromide to 2- hydroxy-5-methoxy benzaldehyde under vigorous measure of moister isolated environment to produce propargyl ether(5-methoxy-2-(prop-2-yn-1-yloxy)benzaldehyde) 3 in which has terminal triple bond. In parallel a glycocyl azide was prepared by applying glycocyl acetate (acetate for protection) via bromination and then substituted by treatment with sodium azide to produce glycocyl azide in which actively reacted with terminated triple bond by click reaction in the present of Cu(II) catalyst. The coupling reaction of terminal alkyle group in compound 3 with azide group of (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate) has given high yield of triazole. The produced triazole molecule is triazole(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(4-((2-formyl-4-methoxy)methyl)-1H-1,2,3-triazole-1-yl)tetrahydro-2H-pyran-3,4,5,-triyacetate) 7 undergoes further reaction to substitute carbonyl of the aromatic with hydrazide by applying 4-methyl-1,2,3-thiadiazole-5-carbohydrazide reagent. The glycocyl acetate was de-esterifide by sodium methoxide to remove the acetate protection. The structure of all these synthesized molecules was confirmed by FTIR, H1NMR, C13 NMR.

SYNTHESIS AND PROPERTIES OF THE DIPROPARGYL DIETER DERIVATIVE 2-BROMINE-2- NITRO-PROPANDIOL-1,3 (BRONOPOL)

The article is devoted to a comprehensive study of 2-bromo-2-nitro- propanediol - 1,3 (bronopol) in order to expand the derivatives of bronopol as food products, preservatives, in all sectors of the national economy. The derivatives of dipropargyl diester 2 - bromo -, 2 - nitro - propanediol - 1,3, γ,γ ́-dicopper (2-bromo-,2-nitro-dipropargyl diester) propanediol-1,3 (II), γ,γ ́-bis- (silver 2-bromo-, 2-nitro-dipropargyl ether) - propanediol-1,3 (III), mercury-bis- (propargyl ether) - 2 - bromo-, 2- nitro-propanediol - 1, 3 (IV), (γ,γ ́-dibromo-dipropargyl diester) - 2- bromo-, 2-nitropropanediol-1,3 (VIII) were synthesized.. We also considered the preparation of γ, γ ́-diiodo-dipropargyl diester - 2-bromo-, 2-nitropropanediol-1,3 (V), bis (4,4 ́-pyrazolyloxymethylene) - 2 - bromo -, 2 - nitro - propanediol - 1.3 (IX). The chemical properties of the 2-bromo-, 2-nitro-, dipropargyl diester of 1,3-propanediol-1,3 were studied, they learned that its −

Self-plasticization of neoprene rubber via click chemistry from environmentally sustainable cardanol

The sustainable biomass cardanol grafting onto neoprene (CR) rubber was carried out successfully at room temperature by covalently binding to CR via click chemistry to realize the internal plasticization of CR rubber. The structure of the synthesized product was characterized by Fourier transform infrared spectroscopy and proton nuclear magnetic resonance, and differential scanning calorimetry and thermogravimetric analysis demonstrate a lowering of the glass transition temperature of the CR-propargyl ether cardanol as compared to CR. This confirms the plasticization effect of the cardanol when grafted onto CR. The cardanol as an internal plasticizer also has a good thermal stability and almost near-zero migration.

Synthesis and optical properties of novel 1,2,3-triazole derivatives possessing highly substituted imidazoles

Reactions of 1,4,5-triaryl-2-(4-bromomethyl)phenyl-imidazoles with sodium azide in acetone give the corresponding azidomethyl derivatives, which on 1,3-dipolar cycloaddition with various terminal alkynes in the presence of CuI afford novel 1,2,3-triazole products. On the other hand, treatment of 2,4,5-triaryl-1-(4-hydroxyphenyl)-imidazoles with propargyl chloride in the presence of a base gives the corresponding propargyl ether derivatives, which under CuI-catalyzed 1,3-dipolar cycloaddition with benzyl azide produce 1,2,3-triazole derivatives. All the products are characterized from their spectroscopic data and most are evaluated for fluorescence emission. The optical parameters of the studied products are also reported.