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Dual fluorescent phenanthridinones and crinasiadine derivatives by consecutive
palladium-catalyzed three-component syntheses
#MMPMID41384065
Kohlbecher R
; Müller TJJ
RSC Adv
2025[Dec]; 15
(57
): 49364-49373
PMID41384065
show ga
The sequential concatenation of Buchwald-Hartwig amination, Suzuki coupling, and
lactamization in a consecutive palladium-catalyzed three-component synthesis
provides direct access to functionalized N-arylsubstituted phenanthridinones and
alkaloid-analogous crinasiadines starting from simple, readily available
ortho-bromoanilines. A modified reaction sequence, consisting of Suzuki coupling,
amide bond formation (lactamization), and subsequent alkylation at the amide
nitrogen, provides N-alkylsubstituted phenanthridinones and crinasiadines,
including two natural products, which are known for their cytotoxic activity
against various cancer cell lines. A comprehensive investigation of the
photophysical properties reveals dual emission of the N-aryl substituted
derivatives, characterized by locally excited states (LE band) and intramolecular
charge transfer states (CT band). Quantum chemical calculations rationalize the
dual emission and suggest that the LE band derives from the pseudo-N-intra
conformation, whereas the CT band arises from the pseudo-N-extra conformation in
the excited state.
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