RESUMEN
The construction of a novel class of indazolo[2,1-a]cinnolin-7-ium and diazabenzofluoranthenium salts was developed by using Rh(iii)-catalyzed C-H activation/annulation reactions with 2-phenyl-2H-indazole, and internal alkynes, which resulted in structurally important polycyclic heteroaromatic compounds (PHAs). This reaction uses mild reaction conditions and has a high efficiency, low catalyst loading, and wide substrate scope. The overall catalytic process involves C-H activation followed by C-C/C-N bond formation. Furthermore, the synthesised cinnolinium/fluoranthenium salts exhibit potential fluorescence properties and 5i was targeted in particular for specific mitochondrial staining in order to investigate cancer cell lines.
Asunto(s)
Fluorenos/síntesis química , Compuestos Heterocíclicos con 2 Anillos/síntesis química , Mitocondrias/química , Orgánulos/química , Rodio/química , Células A549 , Catálisis , Supervivencia Celular/efectos de los fármacos , Teoría Funcional de la Densidad , Fluorenos/química , Compuestos Heterocíclicos con 2 Anillos/química , Compuestos Heterocíclicos con 2 Anillos/farmacología , Humanos , Estructura Molecular , Imagen Óptica , Sales (Química)/síntesis química , Sales (Química)/química , Sales (Química)/farmacologíaRESUMEN
Rhodium catalysed dehydrogenative C-H/N-H functionalization was developed to construct phthalazino[2,3-a]-/indazolo[1,2-a]cinnolines by reacting N-phenyl phthalazine/indazole with alkynes. The synthesized compounds exhibit prominent fluorescence properties in solid and aggregation states. Their application in cell imaging was investigated using various cancer cell lines.
Asunto(s)
Fluorescencia , Compuestos Heterocíclicos con 2 Anillos/síntesis química , Imagen Molecular , Neoplasias/patología , Compuestos Organometálicos/química , Compuestos Organometálicos/síntesis química , Rodio/química , Alquinos/química , Catálisis , Línea Celular Tumoral , Supervivencia Celular , Compuestos Heterocíclicos con 2 Anillos/química , Humanos , Hidrogenación , Indazoles/química , Modelos Moleculares , Estructura Molecular , Neoplasias/diagnóstico , Ftalazinas/químicaRESUMEN
Hypervalent iodonium ylides expeditiously generate carbenes which undergo domino intermolecular C-H activation followed by intramolecular condensation in the presence of N-methoxybenzamide as a starting material and a Rh(iii)-catalyst to afford dihydrophenanthridines. KIE studies and DFT calculations were performed to substantiate the mechanistic pathway. To extend the synthetic utilisation, fluorescent pyranoisocoumarins were achieved by using Rh(iii)-catalyzed peri-C-H/O-H activation/annulation reactions.
RESUMEN
Rhodium-catalysed decarbonylative annulation of isatoic anhydrides with alkynes through C-H activation for the synthesis of aminoisocoumarins was developed. This enables the gram-scale transformation to iodoisocoumarin which is a vital building block in transition-metal-catalysed cross couplings. These compounds exhibit blue-emitting luminescence properties.
RESUMEN
A facile ruthenium(II)-catalyzed regiospecific C-H/O-H oxidative annulation methodology was developed to construct isochromeno[8,1-ab]phenazines. This methodology delivers various advantages, such as scope for diverse substrates, tolerance to a range of functional groups, stability under air, and yields regioselective products. This methodology was successfully applied to synthesize far red (FR) fluorescent probes for live cancer cell imaging. The synthesized compounds displayed notable fluorescence properties in solution and thin-film. Their application in live cancer cell imaging was investigated using various cancer cell lines. The synthesized compound showed prominent FR fluorescence, with high quantum yield, and exhibited better cell-imaging properties, with excellent biocompatibility.