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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
3-(9H-Carbazol-9-yl)-2H-chromen-2-one
Julien Letessier1, Dieter Schollmeyer, Heiner Detert
1University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany.
Abstract:
The title compound, C(21)H(13)NO(2), was prepared as an example of a new synthesis of carbazoles from a cyclic dibenzo-iodo-lium salt via a twofold Pd-catalysed aryl-ation of a primary amine. The two essentially planar π-subsystems [maximum deviations from the mean square plane of 0.038 (2) Å in the carbazole and 0.059 (2) Å in the coumarine unit] open a dihedral angle of 63.05 (4)°. Two mol-ecules form a centrosymmetrical pair connected via π-π inter-actions between the pyrrole and pyrone rings [centroid-centroid distance = 3.882 (1) Å] and one benzene of the carbazole and the pyrone unit [centroid-centroid distance 3.824 (1) Å]. The lattice is stabilized by C-H⋯O bridging to both coumarin O atoms.
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