23592-78-1Relevant academic research and scientific papers
Direct synthesis of N -H carbazoles via iridium(III)-catalyzed intramolecular C-H amination
Suzuki, Chiharu,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
, p. 1597 - 1600 (2015/03/30)
The iridium-catalyzed dehydrogenative cyclization of 2-aminobiphenyls proceeds smoothly in the presence of a copper cocatalyst under air as a terminal oxidant through intramolecular direct C-H amination to produce N-H carbazoles. A similar iridium/copper system can also catalyze the unprecedented dimerization reaction of 2-aminobiphenyl involving 2-fold C-H/N-H couplings.
Synthesis of carbazoles by copper-catalyzed intramolecular C-H/N-H coupling
Takamatsu, Kazutaka,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
supporting information, p. 2892 - 2895 (2014/06/23)
A Cu-catalyzed intramolecular C-H amination for the synthesis of carbazoles has been developed. The key to success is the installation of the picolinamide-based directing group, which is spontaneously removed after the coupling event. The Cu catalysis proceeded smoothly under Pd- and I(III)-free conditions, and its mild oxidation aptitude enables the rapid and concise construction of heteroatom-incorporated carbazole core π-systems.
Triphenylphosphine-mediated reductive cyclization of 2-nitrobiphenyls: A practical and convenient synthesis of carbazoles
Freeman, Adam W.,Urvoy, Marie,Criswell, Megan E.
, p. 5014 - 5019 (2007/10/03)
The synthesis of a series of substituted carbazoles from the corresponding 2-nitrobiphenyl derivatives using a novel modification of the Cadogan reaction is described. Cyclization of the 2-nitrobiphenyls was achieved via reductive deoxygenation of the nitro groups using a slight excess of triphenylphosphine in a suitable solvent. We have observed a temperature dependence on the extent of conversion under these conditions, with higher boiling solvents affording higher yields across a range of substrates. The new reaction conditions are very straightforward and convenient to execute, tolerate a broad range of functional groups, and yield carbazole products in the absence of unwanted side products.
STUDIES ON ENAMIDES PART-2 : A NOVEL PHOTOCHEMICAL SYNTHESIS OF 9H-INDOLOPHENANTHRIDIN-9-ONE, A BENZCANTHINE ANALOGUE
Ghosh, Somnath,Datta, Diptendu Bhusan,Datta, Indira,Das, Tapas Kumar
, p. 3775 - 3786 (2007/10/02)
The synthesis of 3-aroylcarbazoles and the unknown 1-aroylcarbazoles has been achieved by the photolysis of 9-aroylcarbazoles in polar solvent.Irradiation of 3(a-c) in non-polar solvent afforded regiospecifically 5(a-c), carbazole (1) and for the first time, 9H-indolophenanthridin-9-one (8) from 3b.The yield of 8 was significantly improved by UV exposure of 9-(2-iodobenzoyl)-carbazole (3e) in methanol and iodine, without providing any photomigrated product.
