Many steps make light work: substituted phenanthridinones can be obtained with high regioselectivity and in very good yields by palladium-catalyzed cyclization reactions of N-methoxybenzamides with arenes. The reaction proceeds through multiple oxidative C-H activation and C-C/C-N formation steps in one pot at room temperature, and thus provides a simple method for generating bioactive phenanthridinones.
General solution: An efficient rhodium‐catalyzed dual CH bond activation and cyclization of N‐methoxybenzamides 1 with aryl boronic acids 2 (see scheme; Cp*=Me5C5) provides a straightforward and general approach to the phenanthridinone structure, which occurs widely in natural products and drugs. Highly regioselective CC and CN bond formation under mild conditions afforded a wide range of substituted phenanthridinones 3.
A cobalt-catalyzed addition of aryl- and alkenylboronic acids to aldehydes and phthalaldehyde to give the corresponding biarylketones and 3-aryl phthalides in good to excellent yields in one pot is described.
Viele kleine Schritte: Substituierte Phenanthridinone werden mit hoher Regioselektivität und in sehr guten Ausbeuten durch Palladium‐katalysierte Cyclisierungen von N‐Methoxybenzamiden mit Arenen aufgebaut (siehe Schema). Die Reaktion verläuft über mehrere oxidative C‐H‐Aktivierungen unter Bildung von C‐C‐ und C‐N‐Bindungen in einem einzelnen Reaktionsgefäß bei Raumtemperatur und bietet somit einfachen Zugang zu bioaktiven Phenanthridinonen.
New complex of Ni(II) with p-[N,N-bis(2-chloroethyl)]aminobenzaldehyde thiosemicarbazone (CEABTSC) have been synthesized and characterized by elemental analysis, IR, electronic, and 1 H NMR spectroscopy. The crystal structure of the free ligand has been determined by single-crystal X-ray diffraction technique. The compound crystallizes in the Triclinic crystal system with space group P-1, Z D 2, Calculated density D 1.392 mg/m 3 , V D 761.64 (18) A 3 with unit cell parameters a D 8.2847(11) A , a D 99.074 , b D 8.7432(12) A , b D 94.035(7) , c D 11.2423(15) A , g D 107.337 (6) ; final R 1 and wR 2 are 0.0796 and 0.3021, respectively. The crystal structure reveals that the compound exists in the thione form and C12 and C11 are at E configuration to each other with respect to N2-N3 bond. The packing of the molecules in the crystal lattice is stabilized by intramolecular N(3)-H(3). . .S(1) and N(4)-H(4D). . . S(1) hydrogen bonds resulting in the formation of edge fused R 2 2 (8) ring motif. In the complex, thiosemicarbazone ligand is coordinated to nickel through (1:2 complex) SNNS mode. The complex has been tested for their antibacterial activity against various pathogenic bacteria.
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