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Relevant academic research and scientific papers

Highly Efficient Iridium-Based Photosensitizers for Thia-Paternò-Büchi Reaction and Aza-Photocyclization

Substrates in excited state differ significantly from the corresponding ground state so that they are treated as different chemical species with diverse physical properties and chemical reactivity. Therefore, applying photocatalytic systems to activate substrates becomes increasingly popular. Although photosensitizers serve as the core of the photocatalytic reaction, the design of a photosensitizer has not been taken for granted. By modifying ligands of organometallic complexes to optimize properties of photosensitizers, we successfully achieved a series of iridium complexes with long excited triplet-state lifetime, high triplet excited-state energy, strong absorption, and robust stability. The efficacies of the prepared iridium complexes as photosensitizers were evaluated toward various challenging photocycloaddition reactions (e.g., thia-Paternò-Büchi reaction and multicomponent one-pot aza-photocyclization) between heterocyclic compound maleimides and unsaturated moieties that are not efficient to complete with well-established photosensitizers.

Redox-Selective Iron Catalysis for α-Amino C-H Bond Functionalization via Aerobic Oxidation

Single-electron oxidation and α-deprotonation of tertiary anilines using Fe(phen)3(PF6)3 afford α-aminoalkyl radicals, which can be coupled with electrophilic partners to afford various tetrahydroquinolines. Mechanistically, the Fe(phen)n 2+/3+ catalytic cycle is maintained by O2 or a TBHP oxidant, and the presence of the oxygen bound iron complex, Fe(III)-OO(H), was elucidated by electron paramagnetic resonance and electrospray ionization mass spectrometry. This redox-selective nonheme iron catalyst behaves similarly to bioinspired heme iron catalysts.

Pyrrolo[3,4-c]quinoline-1,3-dione derivatives and synthesis method thereof

The present invention relates to a synthesis method of a pyrrolo[3,4-c]quinoline-1,3-dione derivative, wherein different kinds of pyrrolo[3,4-c]quinoline-1,3-dione derivatives representing various biological activities can be manufactured with a high yield through one step reaction using a low-priced nonmetallic catalyst under a mild condition.COPYRIGHT KIPO 2015

Microwave-assisted synthesis of diverse pyrrolo[3,4- c ]quinoline-1,3- diones and their antibacterial activities

With the aim of developing a general and practical method for library production, a novel and efficient two-phase microwave-assisted cascade reaction between isatins and β-ketoamides in [Bmim]BF4/toluene was developed for the synthesis of pyrrolo[3,4-c]quinoline-1,3-diones. The features of this methodology are, the use of microwave-assisted rapid synthesis, mild reaction conditions, high yields, operational simplicity, facile product separation, and recyclability. Furthermore, the antibacterial activities of the pyrrolo[3,4-c]quinoline-1,3-dione derivatives produced were evaluated against Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Enterobacter aerogenes) and Gram-positive bacteria (Bacillus cereus and Staphylococcus aureus). These derivatives showed antibacterial activities against Gram-positive strains that were at least equivalent to that against Gram-negative strains. Compound 7{3,5} displayed the most potent antibacterial activity against P. aeruginosa (MIC = 0.5 μg/mL) and greater activity than standard ampicillin (MIC = 1 μg/mL). Compound 7{4,7} exhibited the best inhibitory activity against E. coli and E. aerogenes (MIC = 1 and 0.5 μg/mL), compared with the standard ampicillin (both MICs = 1 μg/mL). The synthesized pyrrolo[3,4-c]quinoline-1,3-diones are expected to be widely used as lead compounds for the development of new antibacterial agents.

Sonochemically synthesized ferromagnetic Fe3O4 nanoparticles as a recyclable catalyst for the preparation of pyrrolo[3,4-c]quinoline-1,3-dione derivatives

This paper reports the green, rapid synthesis of Fe3O4 nanoparticles by the ultrasonic irradiation of Fe2O3 solution and Perilla frutescens (P. frutescens) leaf extract, which was used as both reducing and capping agent. The synthesized Fe3O4 nanoparticles were characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray analysis, vibrating sample magnetometry, thermogravimetric analysis (TGA) and X-ray photoelectron spectroscopy (XPS). The FT-IR spectra indicated that the bioactive molecules present in the plant extract contain polyols, which act as a reducing as well as capping agent, as confirmed by TGA. TEM and SEM showed that the Fe3O4 nanoparticles were approximately spherical in shape with a mean size of 50 nm. The synthesized Fe3O4 nanoparticles exhibited ferromagnetic behavior with a saturation magnetization of 25.15 emu g-1. The Fe3O4 nanoparticles, with their easy recovery by an external magnetic field, exhibited strong catalytic activity towards pyrrolo[3,4-c]quinoline-1,3-dione derivatives. These results suggest that the Fe3O4 nanoparticles produced can be applied as a catalyst in organic synthesis and recycled at least five times without significant loss in its activity.

Efficient one-step synthesis of pyrrolo[3,4-c]quinoline-1,3-dione derivatives by organocatalytic cascade reactions of isatins and β-ketoamides

We describe an efficient one-step synthesis of pyrrolo[3,4-c]quinolinedione derivatives using ethylenediamine diacetate (EDDA)-catalyzed cascade reactions of isatins and β-ketoamides. It is the first direct conversion of isatins to pyrrolo[3,4-c]quinolinedione derivatives via C-N bond cleavage and isatin ring expansion. Furthermore, this reaction provides a one-step synthetic route for the production of biologically interesting complex molecules that are generally prepared using multi-step reactions.

Synthesis and Reactions of 3-(N-Arylcarbamoyl)-2-methylcinchoninic Acid

The Pfitzinger reaction between acetoacetic acid arylamides and the potassium salt of isatinic acid leads in good yield to 3-(N-arylcarbamoyl)-2-methylcinchoninic acids.Refluxing the latter in 2-propanol produced N-substituted imides of 2-methylquinoline-