I2/DMSO-Promoted the synthesis of chromeno[4,3‑b]quinolines through an imine formation/aza-Diels-Alder/aromatization tandem reaction under metal-catalyst and photosensitizer-free conditions

A tandem approach was developed for the efficient synthesis of substituted chromeno[4,3-b]quinolines from arylamines and O-cinnamyloxy salicylaldehydes under metal-catalyst and photosensitizer-free reaction conditions. Our protocol is based on an inexpensive I2/DMSO system in which molecular iodine first acts as a Lewis acid to promote the formation of the corresponding imine bearing the alkene moiety, then, this species fulfills a second role by catalyzing the intramolecular aza-Diels-Alder cycloaddition to generate the respective tetrahydro-chromenoquinolines as an intermediates. Finally, the dual behaviour of DMSO as an oxidant and as a solvent resulted crucial at this stage, allowing the regeneration of I2 and promoting the aromatization of the tetrahydro-chromenoquinoline intermediates to yield the desired 7-aryl-6H-chromeno[4,3-b]quinolines. This protocol features by being mild, easy to perform, high step-economy (tandem process) and for providing a new access to biologically important nitrogen and oxygen containing heterocyclic molecules.

Electrical and Electrochemical Studies of Polymer Gel Electrolytes Based on Agarose-LiBOB and P(VP-co-VAc)-LiBOB

This study focuses on preparation and characterization of polymer gel electrolytes (PGEs) based on agarose–LiBOB–DMSO and poly(1-vinylpyrrolidone-co-vinyl acetate)–LiBOB–DMSO. Two systems of PGEs were prepared by dissolving a different amount (1-8 wt.%) of agarose and (1-8 wt.%) P(VP-co-VAc) as host polymer in 0.8 M of LiBOB–DMSO solution. The addition of host polymer into 0.8 M of LiBOB–DMSO solution will result an optimum conductivity which is 6.91 x 10-3 S.cm-1 for agarose–LiBOB–DMSO system and 7.83 x 10-3 S.cm-1 for P(VP-co-VAc)–LiBOB–DMSO system. In the temperature range of conductivity studies discovered that the agarose–LiBOB–DMSO and P(VP-co-VAc)–LiBOB–DMSO polymer gel electrolytes abide by Arrhenius rule indicating that this PGEs could run at elevated temperature conditions. Furthermore, lithium transference number confirms that both electrolyte systems have 0.03 and 0.12 respectively at room temperature (298 K). Linear sweep voltammetry (LSV) measurements demonstrate the agarose–LiBOB–DMSO system has a potential of 4.26 V and P(VP-co-VAc)–LiBOB–DMSO system has a potential of 4.50 V which is good in electrochemical stability.

Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles

An efficient method for the synthesis of pharmaceutically prospective pyrrole–aminopyrimidine ensembles (in up to 91% yield) by the cyclocondensation of easily available acylethynylpyrroles with guanidine nitrate has been developed. The reaction proceeds under heating (110–115 °C, 4 h) in the KOH/DMSO system. In the case of 2-benzoylethynylpyrrole, the unexpected addition of the formed pyrrole–aminopyrimidine as N- (NH moiety of the pyrrole ring) and C- (CH of aminopyrimidine) nucleophiles to the triple bond is observed.

2-Aryl-Perfluorobenzoxazoles: Synthesis, Fluorescence Properties and Synthetic Application in Cubic Platinum Nanoparticles

A simple and efficient methodology for the synthesis of 2-aryl-perfluorobenzoxazoles was developed via a direct dual C-F functionalization of perfluorobenzene with arylformamide in the presence of Fe(II)/NaH/DMSO system. Various substituted...

Highly Functionalized Pyrrolylpyridines from 2-(Acylethynyl)-pyrroles

A novel family of pharmaceutically prospective, densely functionalized (aryl-, hetaryl-, acyl-, and vinyl-substituted) pyrrolylpyridines has been assembled in up to 95% yields via the amination (NH4Cl/K2CO3/DMSO system, 90 °C, 16 h) of 2-(acylethynyl)pyrroles, followed by cyclization (MeOH, reflux, 6 h, up to 90% yield) of the formed intermediate 1-(pyrrol-2-yl)-1-aminoenones with acetylenic ketones (Bohlmann–Rahtz reaction). The intermediate pyrrolyl aminodienones, prospective building blocks for organic synthesis, can be separately synthesized (DMSO, 90 °C, 6 h) in 70–86% yields. A novel facet of this chemistry is stereoselective synthesis of C-vinylated pyridines, (E)-3-[5-acyl-2-aryl-6-(pyrrol-2-yl)pyridin-3-yl]-1-arylprop-2-en-1-ones, by involving the second molecule of acylacetylene into the reaction.

Dimethyl sulfoxide as a strongly coordinating solvent: 3′,4′-dihydroxyflavone-Cu(II)-DMSO system case study

Dimethyl sulfoxide (DMSO) is an aprotic organic solvent widely used in laboratory practice due to its ability to dissolve both polar and nonpolar compounds. However, DMSO is also commonly known as a strongly coordinating solvent, especially towards transition metal containing complexes. In this study, estimation of the coordination ability of DMSO towards the Cu(II) ion was attempted, employing a model system composed of 3′,4′-dihydroxyflavone-Cu(II) complex in the presence of explicit DMSO molecules, using the density functional theory (DFT). Nature of the Cu-DMSO chemical interaction (i.e. Cu-O bonding) was studied within the framework of quantum theory of atoms in molecules (QTAIM). Impact of DMSO coordination on the charge and spin distribution at Cu(II) ion was inspected using Mulliken population and QTAIM analysis.