Pyridyl-substituted 1,3,5-triazines were synthesized in good to excellent yields via an unprecedented one-step cyclocondensation of 4H-pyrido[1,3]oxazin-4-ones with amidines at room temperature or under microwave irradiations. The broad applicability was demonstrated by 33 examples with a variety of amidines and three different 4H-pyrido[1,3]oxazin-4-one chemical series. In addition, a one-pot process from 4H-pyrido[1,3]oxazin-4-one precursors (imide sodium salts) was developed and led to the desired triazines compounds, thus allowing a one-step economy in their global synthetic preparation. This approach provides rapid access to pyridyl (or pyridone)-substituted 1,3,5-triazines with high potential in various fields of application.
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http://dx.doi.org/10.1021/jo5010668 | DOI Listing |
J Med Chem
January 2025
Sorbonne Université, CNRS Institut Parisien de Chimie Moléculaire, IPCM, F-75005 Paris, France.
Despite recent advances in cancer treatment, there is still a need for novel compounds with antineoplastic activity. Among 11 biphenyl-based organogold(III) -heterocyclic carbene (NHC) (BGC) complexes of general formula [(C^C)Au(NHC-pyr)X], where (C^C) = 4,4'-ditertbutylbiphenyl, X = Cl or phenylacetylide, and (NHC-pyr) is a pyridyl-substituted NHC ligand, the complex bearing a 4-CF-pyridyl substituent and a chloride ligand showed promising antineoplastic activity on the triple negative breast cancer cell line. was able to induce cell apoptosis but had no effect on the cell cycle.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse 4, 35043 Marburg, Germany.
A new approach is introduced to control the metal-centred configuration of stereogenic-at-iron catalysts by utilizing axial ligand chirality, which becomes locked upon metal coordination. This strategy is applied to an iron catalyst containing two chelating -(2-pyridyl)-substituted triazol-5-ylidene mesoionic carbenes (MICs) resulting in a helical topology with a stereogenic iron centre.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, Institute of Luminescent Materials and Information Displays, College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021, China.
The advancement of tin-based perovskite solar cells (TPSCs) has been severely hindered by the poor controllability of perovskite crystal growth and the energy level mismatch between the perovskite and fullerene-based electron transport layer (ETL). Here, we synthesized three cis-configured pyridyl-substituted fulleropyrrolidines (PPF), specifically 2-pyridyl (PPF2), 3-pyridyl (PPF3), and 4-pyridyl (PPF4), and utilized them as precursor additives to regulate the crystallization kinetics during film formation. The spatial distance between the two pyridine groups in PPF2, PPF3, and PPF4 increases sequentially, enabling PPF4 to interact with more perovskite colloidal particles.
View Article and Find Full Text PDFJ Mater Chem B
November 2024
Department of Chemical and Materials Engineering, Photo-sensitive Material Advanced Research and Technology Center (Photo-SMART), National Kaohsiung University of Science and Technology, Kaohsiung 80778, Taiwan.
Hydrogen sulfide (HS) is a critical bioregulator implicated in numerous physiological and pathological processes, including cancer and neurodegenerative diseases. Compared with traditional instrument analysis, fluorescence detection technology based on small molecules in real-time and sensing HS has attracted attention. In this investigation, we developed a system of coumarin-based fluorophores linked with aminopyridine a dipolar imino-double bond.
View Article and Find Full Text PDFChemistry
December 2024
Department of Chemistry and Research Center for Smart Molecules, Rikkyo University, 3-34-1 Nishi-Ikebukuro, Toshima-ku, Tokyo, 171-8501, Japan.
As a new molecular scaffold of photoswitchable fluorophore, we developed a photochromic diarylethene containing a betaine structure based on pyridinium N-enolate. A facile reaction of a pyridyl-substituted dithienylperfluorocyclopentene derivative with octafluorocyclopentene constructed the betaine structure. The introduction of the betaine moiety provided the diarylethene molecule with bathochromically shifted optical absorption and fluorescing ability, thus enabling the molecule to function as a visible-light-responsive turn-off mode photoswitchable fluorophore.
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