A5060055418- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Catalytic C–H Functionalization Methods
- Luminescence and Fluorescent Materials
- Catalytic Cross-Coupling Reactions
- Multicomponent Synthesis of Heterocycles
- Catalytic Alkyne Reactions
- Synthesis and Biological Evaluation
- Synthetic Organic Chemistry Methods
- Click Chemistry and Applications
- Chemical Synthesis and Analysis
- Phenothiazines and Benzothiazines Synthesis and Activities
- Organic Light-Emitting Diodes Research
- Asymmetric Synthesis and Catalysis
- Porphyrin and Phthalocyanine Chemistry
- Radical Photochemical Reactions
- Oxidative Organic Chemistry Reactions
- Cyclopropane Reaction Mechanisms
- Synthesis and Characterization of Pyrroles
- Photochromic and Fluorescence Chemistry
- Molecular Junctions and Nanostructures
- Sulfur-Based Synthesis Techniques
- Synthesis and Reactivity of Heterocycles
- Photochemistry and Electron Transfer Studies
- Synthesis of Organic Compounds
Heinrich Heine University Düsseldorf
2016-2025
Chemnitz University of Technology
2008-2023
Karlsruhe Institute of Technology
2016-2022
Slovak University of Technology in Bratislava
2021
Nara University of Education
2021
Mokpo National University
2021
Kunming University of Science and Technology
2021
Wuyi University
2021
Zhengzhou University
2021
Sun Yat-sen University
2021
[reaction: see text] TMS-ynones are versatile synthetic equivalents of beta-keto aldehydes and can be readily synthesized in an atom-economical fashion by coupling (het)aroyl chlorides (TMS)-acetylene with only one equiv (!) triethylamine under Sonogashira conditions. This mild ynone synthesis is also a suitable entry to 2,4-disubstituted pyrimidines the sense one-pot three-component reaction, i.e., coupling-addition-cyclocondensation sequence.
In one go: (Hetero)aryl iodides, alkynes, carbon monoxide, and amidines can be assembled in a consecutive four-component reaction to give pyrimidines by sequence of carbonylative alkynylation cyclocondensation. Carbonylative also is the key step two-step syntheses meridianins meridianin derivatives.
Abstract The copper‐catalyzed alkyne‐azide cycloaddition (CuAAC) is a highly versatile, regioselective synthesis of 1,4‐disubstituted 1,2,3‐triazoles under mild reaction conditions and has found numerous applications in medicinal, bioorganic, materials chemistry the past one half decades. By virtue enormous tolerance for functional groups conditions, CuAAC become increasingly important combination with multicomponent reactions (MCR), either domino or consecutive fashion. While majority...
Abstract 3,5‐Disubstituted and 1,3,5‐trisubstituted pyrazoles are readily synthesized from acyl chlorides, terminal alkynes, hydrazines by a consecutive one‐pot three‐component Sonogashira coupling/Michael addition/cyclocondensation sequence in good to excellent yields. These highly fluorescent, both solution the solid state. Investigation of electronic properties UV/Vis fluorescence spectroscopy DFT ZINDO CI computations reveal that excited state is polar allows fine‐tuning absorption...
Abstract Quinoxalines represent bicyclic nitrogen‐containing heterocycles with a wide array of applications. They exhibit multitude biological activities relevant in medicinal chemistry as well plethora luminescence properties. Quinoxaline syntheses exploit the whole raft multicomponent from domino to sequential or consecutive reactions, harvesting well‐known synthetic concepts and such Ugi‐reactions, but also leading development novel reactions sequences. Diversity‐oriented synthesis...
A key feature of cancer is the disruption cell cycle regulation, which characterized by selective and abnormal activation cyclin-dependent kinases (CDKs). Consequently, targeting CDKs via meriolins represents an attractive therapeutic approach for therapy. Meriolins represent a semisynthetic compound class derived from meridianins variolins with known CDK inhibitory potential. Here, we analyzed two novel derivatives meriolin 16 36 in comparison to other potent inhibitors could show that they...
1,2,3,5-Tetrasubstituted pyrroles can be synthesized in good yields a one-pot, three-step, four-component process by coupling−isomerization−Stetter reaction−Paal−Knorr sequence of an electron-poor (hetero)aryl halide, terminal propargyl alcohol, aldehyde, and primary amine. The structures the 1,4-diketone 4f pyrrole 6b were additionally supported X-ray structure analyses.
Four bonds at one stroke and products with intensive fluorescence result from a domino sequence consisting of insertion, coupling, isomerization, Diels–Alder steps (see scheme, Ts=tosyl). Alkynoyl ortho-iodophenyl esters or N-(iodophenyl)alkynanilides 1 react propargyl allyl ethers 2 to furnish spirocycles 3.
We report the synthesis and characterization of five novel phenothiazine-containing cruciforms (5-9). The targets were prepared by a NaH-promoted Horner reaction tetraethyl(2,5-diiodo-1,4-phenylene)bis(methylene)diphosphonate with 10-hexyl-10H-phenothiazine-3-carbaldehyde. formed intermediary 3,3'-(1E,1'E)-2,2'-(2,5-diiodo-1,4-phenylene)bis(ethene-2,1-diyl)bis(10-hexyl-10H-phenothiazine) was reacted several different aromatic alkynes (1-tert-butyl-4-ethynylbenzene,...
Starting from N-hexylphenothiazine, a versatile construction kit of brominated and borylated phenothiazines can be easily prepared by sequence bromination, bromo-lithium exchange/borylation, Suzuki coupling. Subsequent arylation the building blocks gives soluble, monodisperse, structurally well defined oligophenothiazines in good yields. The molecular weights at peak maximum (Mp), obtained GPC (gel permeation chromatography), actual oligomer series, mass spectrometry, show excellent...
Alkynones are versatile three-carbon building blocks in heterocyclic chemistry. They easily and efficiently prepared by a modified Sonogashira coupling of acid chlorides terminal alkynes. As consequence the mild reaction conditions stage is set for new diversity-oriented routes to heterocycles sequential consecutive transformations. Hence, isoxazoles, indolizines, pyrazoles, pyridimines, 1,5-benzoheteroazepines, furans, oxazoles, pyrroles, tetrahydro- β-carbolines, 4H-thiochromen-4-ones...
An alkynoyl ortho-iodo phenolester or anilides and propargyl allyl ethers react under Sonogashira coupling conditions in the sense of an insertion-coupling-isomerization-Diels-Alder hetero domino reaction to furnish (tetrahydroisobenzofuran)-spirobenzofuranones -spirodihydroindolones good yields. Many representatives can be crystallized single crystal structure analyses display steric electronic substituent effects on torsional angles terminal (hetero)aryl groups central cis,trans-butadiene...
1,3,4,5-Tetrasubstituted pyrazoles can be rapidly and efficiently synthesized in a one-pot, four-step sequence consisting of Sonogashira coupling, addition-cyclocondensation, bromination, Suzuki coupling. The second the last step are microwave-assisted, according to sequential catalysis, no addition further Pd catalyst is needed for terminal step. title compounds show intense blue fluorescence high quantum yields.
(Hetero)aryl-, alkenyl-, and selected alkyl-substituted acid chlorides can be efficiently coupled with N-Boc-protected propargylamine to produce ynones which are converted in a one-pot fashion 2-substituted N-Boc-4-iodopyrroles. Upon addition of further alkyne, another Sonogashira coupling carried out fashion. This sequentially Pd/Cu-catalyzed process represents very mild efficient entry 2,4-disubstituted N-Boc-pyrroles.
Alkynones are prominent three-carbon building blocks in heterocyclic chemistry.They can be generated very easily and efficiently by modified Sonogashira coupling of acid chlorides terminal alkynes.Mild reaction conditions now set the stage for new diversity-oriented routes to heterocycles sequential consecutive transformations.Hence, isoxazoles, indolizines, pyrazoles, pyridimines, 1,5-benzoheteroazepines, furans, oxazoles, tetrahydro-β-carbolines accessible coupling-cycloaddition or...
Abstract Functional π-electron systems can be synthesized in a diversity-oriented fashion by applying multicomponent and domino reactions. Based upon alkyne activation Sonogashira coupling, reactive triple or double bonds become the key functionality for sequential consecutive synthesis of heterocycles, such as β-amino vinyl nitrothiophenes, δ-amino propenylidene indolones, indolizines, furans, pyrroles, annelated 2-amino pyridines, spirocyclic benzofuranones indolones. All these...
Phenothiazinyl rhodanylidene acetic acid merocyanine dyes with variable substitution pattern on the peripheral benzene ring were synthesized in good to excellent yields by Knoevenagel condensation of corresponding phenothiazinyl aldehydes and rhodanine-N-acetic acid. The electronic properties investigated cyclic voltammetry, absorption, fluorescence spectroscopy. Electron releasing leads an appreciable lowering oxidation potential, bathochromic shift absorption band, minimization emission...
Breaking the bottleneck: α-Keto carboxylic acids and N-heterocyclic are activated in situ with oxalyl chloride then catalytically alkynylated to give ynediones ynones efficiently a one-pot fashion. 5-Acylpyrazoles 2-phenylaminopyrimidines, potentially interesting for pharmaceutical applications, readily synthesized concise one-pot, three-component syntheses.
2-Substituted 3-ethynylquinoxalines can be rapidly synthesized in generally excellent yields by a consecutive four-component synthesis starting from electron-rich π-nucleophiles, oxalyl chloride, terminal alkynes, and 1,2-diaminoarenes. The title compounds are highly fluorescent with pronounced emission solvatochromism. photophysical properties electronic structure were additionally corroborated computations on the DFT level of theory.
A novel retrosynthetic approach to 3,5-diaryl-2-pyrazolines is provided by a three-component, one-pot reaction initiated palladium/copper-catalyzed cross-coupling (see scheme). The initially formed enone cyclocondenses in situ with the hydrazine furnish heterocycle. EWG=electron-withdrawing group.