443303-81-9Relevant academic research and scientific papers
A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A
Yan, Qiao,Gin, Emma,Wasinska-Kalwa, Malgorzata,Banwell, Martin G.,Carr, Paul D.
, p. 4148 - 4159 (2017)
The title natural products 2-7 have been prepared by reductive cyclization of the relevant 2-arylcyclohex-2-en-1-one (e.g. 20) to the corresponding tetrahydrocarbazole and dehydrogenation (aromatization) of this to give the target carbazole (e.g. 4). Compounds such as 20 were prepared using a palladium-catalyzed Ullmann cross-coupling reaction between the appropriate 2-iodocyclohex-2-en-1-one and o-halonitrobenzene.
A METHOD OF INDOLE SYNTHESIS
-
Page 22, (2008/06/13)
The present invention relates to methods for the synthesis of indoles. In particular, the invention relates to the coupling of an a-haloenone or a-haloenal with an ortho-halonitroarene to form an ortho-(enone)nitroarene or ortho-(enal)nitroarene. Reductive cyclization of an ortho-(enone)nitroarene or ortho-(enal)nitroarene affords access to indole compounds.
Palladium-catalyzed synthesis of 1,2-dihydro-4(3H)-carbazolones. Formal total synthesis of murrayaquinone A
Scott, Tricia L.,S?derberg, Bj?rn C. G.
, p. 6323 - 6332 (2007/10/03)
Two sequential palladium-catalyzed reactions are the key steps in a novel synthetic route to 1,2-dihydro-4(3H)-carbazolones. The steps are an intermolecular Stille cross-coupling followed by a reductive N-heteroannulation. A formal total synthesis of murrayaquinone A, employing this sequence, is reported.
Synthesis of indoles via palladium[0]-mediated ullmann cross-coupling of o-halonitroarenes with α-halo-enones or -enals
Banwell, Martin G.,Kelly, Brian D.,Kokas, Okanya J.,Lupton, David W.
, p. 2497 - 2500 (2007/10/03)
(Matrix presented) Palladium[0]-mediated Ullmann cross-coupling of o-halonitrobenzene (1) and various related nitroarenes with a range of α-halo-enones (e.g., 2) or -enals readily affords the expected α-arylenones, e.g., 3, or -enals, which are converted into the corresponding indoles, e.g., 4, on reaction with dihydrogen in the presence of Pd on C.
Novel palladium-catalyzed synthesis of 1,2-dihydro-4(3H)-carbazolones
Scott, Tricia L.,S?derberg, Bj?rn C.G.
, p. 1621 - 1624 (2007/10/03)
Two sequential palladium-catalyzed reactions are the key steps in a novel synthetic route to carbazolones, an intermolecular Stille coupling followed by a recently developed palladium-catalyzed reductive N-heteroannulation. A number of functionalized 1,2-dihydro-4(3H)-carbazolones were prepared using this sequence.
