Synthesis of 6-(2’ or 4’- nitrophenyl)benzo[b]thiophenes by Palladium-catalyzed cross-coupling

The palladium-catalyzed cross-coupling reactions of organoboron compounds are very useful for carbon-carbon bond formation. Compounds 1 were synthesized by a palladium-catalyzed cross-coupling of bromo or iodonitrobenzenes with boronic esters 2, which were prepared from methylated 6- bromobenzo[b]thiophenes2 by halogen-metal exchange and transmetalation. The intermediates esters 2 were not isolated but directly, after evaporation of the ether, coupled in acetone/water using palladium acetate in the presence of sodium hydrogencarbonate. Yields of isolated compounds 1 were about 40%

Synthesis of diarylamines in the benzo[b]thiophene series bearing electron donating or withdrawing groups

The synthesis of diarylamines has attracted a great deal of interest due to their importance in diverse fields as natural biological active products and analogues, photography and materials science. Herein we report the synthesis of diarylamines 1 bearing electron donating or withdrawing groups by palladium catalyzed amination, in good yields (50%-quantitative yield) using two different bases and choosing the right components

A DMAP-catalyzed mild and efficient synthesis of 1,2-dihydroquinazolines via a one-pot three-component protocol

International audienceAn efficient and simple method for the synthesis of 1,2-dihydroquinazolines catalyzed by 4-(N,N-dimethylamino) pyridine (DMAP) from readily available aromatic or heteroaromatic aldehydes, 2-aminobenzophenone, and ammonium acetate under mild conditions is described. The scope and limitations of the method are discussed

Palladium-catalyzed amination of electron-rich or poor benzo[b]thienyl bromides

Recently we have applied the palladium-catalyzed amination to the synthesis of ortho-bromodiarylamincs in the benzo[blthiophene series . Here we describe the application of this methodology to the amination of electron-rich or poor 3-bromobenzo[b}thiophcnes, using the same conditions for both cases

Inverse Scattering for Gratings and Wave Guides

We consider the problem of unique identification of dielectric coefficients for gratings and sound speeds for wave guides from scattering data. We prove that the "propagating modes" given for all frequencies uniquely determine these coefficients. The gratings may contain conductors as well as dielectrics and the boundaries of the conductors are also determined by the propagating modes.Comment: 12 page

Daniellia oliveri (Rolfe) Hutch and Dalziel : Antimicrobial Activities, Cytotoxicity Evaluation, and Phytochemical Identification by GC-MS

During a previous study that identified plants used in traditional medicine in Togo to treat infectious diseases, Daniellia oliveri was specifically reported to treat intertrigo and candidiasis. Consequently, to explore the anti-infective potential of this plant, we investigated the antibacterial and the antifungal activity of the plant’s parts, as well as the cytotoxic activities of raw extracts and subsequent fractions, and the chemical composition of the most active fractions. In order to evaluate the antimicrobial activity, MICs were determined using the broth dilution method. Then, the most active fractions were evaluated for cytotoxicity by using normal human cells (MRC-5 cells) via the MTT assay. Finally, the most active and not toxic fractions were phytochemically investigated by GC-MS. Interestingly, all the raw extracts and fractions were active against the bacteria tested, with MICs ranging from 16 µg/mL to 256 µg/mL, while no antifungal activity was observed at 256 µg/mL, the highest tested concentration. Moreover, no toxicity was observed with most of the active fractions. The subsequent chemical investigation of the most interesting fractions led to identifying terpenes, phytosterols, phenolic compounds, and fatty acids as the main compounds. In conclusion, this study demonstrated that D. oliveri possesses valuable antibacterial activities in accordance with traditional use

Evaluation of the antioxidant properties of diarylamines in the benzo[b]thiophene series by free radical scavenging activity and reducing power

The antioxidant properties of substituted diarylamines in the benzo[b]thiophene series were evaluated by their reducing power and free radical scavenging activity. The results were compared with those of standards: acid ascorbic for the first method and BHA and BHT for the second. For both methods it was possible to establish some structure–activity relationships (SARs) based on the position of the arylamination on the benzo[b]thiophene moiety, the presence of different substituents on the phenyl ring (F, 1 or 2 OMe) and on the thiophene ring (H, CO2Et, CO2H)

Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesicles

The first thieno-δ-carboline (6,8,9-trimethyl-5H-pyrido[3,2-b]thieno[3,2-f]indole) was prepared in good yield (70%) by intramolecular palladium-assisted cyclization of an ortho-chlorodiarylamine. The latter was in turn selectively synthesized in high yield (90%) by C–N palladiumcatalyzed cross-coupling of 3-bromo-2-chloropyridine with, the also prepared, 6-amino-2,3,7-trimethylbenzo[b]thiophene. Fluorescence studies in solution show that thieno-δ-carboline has a solvatochromic behaviour. Despite the low fluorescence quantum yields in solution, studies of its incorporation in lipid vesicles of DPPC, DOPE and DODAB indicate that thienocarboline is located mainly inside the lipid bilayer, exhibiting different behaviours in gel or liquid-crystalline phases. Our studies are useful for the incorporation of thienocarboline in liposomes and for controlled drug release assays, due to its biological activity

Tandem palladium-catalyzed borylation and Suzuki coupling (BSC) to thienocarbazole precursors

Substituted 2-methyl-2 -nitro diaryl compounds in the benzo[b]thiophene series were prepared by palladium-catalyzed, two-step, one-pot borylation/Suzuki coupling (BSC) reaction in good to high yields. The borylation reaction was performed on methylated 6-bromobenzo[b]thiophenes using pinacolborane and was followed by in situ Suzuki coupling with substituted (CF3, OMe) 2-bromonitrobenzenes. The compounds obtained were cyclized to the corresponding ring A substituted thienocarbazoles which can have biological activity or/and be used as biomarkers due to their fluorescence properties and possible DNA intercalation.Thanks are due to the Foundation for Science and Technology, IBQF, University of Minho (Portugal), to the Research Incitment Programme of the Calouste Gulbenkian Foundation (Portugal) for financial support and to the Escola Superior Agra ´ria, Instituto Polite ´cnico de Braganc ¸a for supporting in part I.C.F.R.F. (Ph.D.).info:eu-repo/semantics/publishedVersio