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Keywords = glycoborine

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18 pages, 330 KB  
Article
Palladium-Catalyzed Synthesis of Natural and Unnatural 2-, 5-, and 7-Oxygenated Carbazole Alkaloids from N-Arylcyclohexane Enaminones
by Rafael Bautista, Pablo A. Montoya, Araceli Rebollar, Eleuterio Burgueño and Joaquín Tamariz
Molecules 2013, 18(9), 10334-10351; https://doi.org/10.3390/molecules180910334 - 26 Aug 2013
Cited by 28 | Viewed by 9812
Abstract
A palladium-catalyzed synthesis of the carbazole framework is described, including the preparation of 2-, 5-, and 7-oxygenated natural and unnatural carbazole alkaloids. A series of N-arylcyclohexane enaminones, generated by condensation of cyclohexane-1,3-dione with diverse anilines, were aromatized by a Pd(0)-catalyzed thermal treatment [...] Read more.
A palladium-catalyzed synthesis of the carbazole framework is described, including the preparation of 2-, 5-, and 7-oxygenated natural and unnatural carbazole alkaloids. A series of N-arylcyclohexane enaminones, generated by condensation of cyclohexane-1,3-dione with diverse anilines, were aromatized by a Pd(0)-catalyzed thermal treatment to afford the corresponding diarylamines. The latter were submitted to a Pd(II)-catalyzed cyclization and methylation processes to provide the desired carbazoles, including clausine V. Following an inverse strategy, a new and short total synthesis of glycoborine is also reported. Full article
(This article belongs to the Special Issue Palladium Catalysts)
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