6286-54-0Relevant academic research and scientific papers
Synthesis of 1,2,3,4-tetrahydrocarbazoles and related tricyclic indoles
Scott, Tricia L.,Burke, Nicholas,Carrero-Martínez, Grissell,S?derberg, Bj?rn C.G.
, p. 1183 - 1190 (2007/10/03)
Reduction of 2-(2-nitrophenyl)-2-cyclohexene-1-ones using palladium on carbon under 1 atm of hydrogen gas at ambient temperature affords 1,2,3,4-tetrahydrocarbazoles in excellent isolated yields. The starting materials were prepared by intermolecular Stille coupling of 2-iodo-2-cyclohexen-1-ones with 2-(tributylstannyl)-1-nitrobenzenes.
Total Synthesis of (-)-Alloaristoteline, (-)-Serratoline, and (+)-Aristotelone
Stoermer, Doris,Heathcock, Clayton H.
, p. 564 - 568 (2007/10/02)
The Aristotelia alkaloids (-)-alloaristoteline (4), (-)-serratoline (12), and (+)-aristotelone (13) have been prepared as summarized in Scheme IV.Thus, via the method of Stevens, (1S)-(-)-β-pinene (9) and 3-indolylacetonitrile (10) were coupled by a Hg(NO3)2-mediated Ritter reaction followed by reduction of the resulting imine to give (+)-makomakine (11).An intramolecular Friedel-Crafts reaction delivered (+)-aristoteline (3), which was oxidized by reaction with oxygen and platinum.Reduction of the intermediate hydroperoxide delivered alkaloid 12.Base-catalyzed skeletal rearrangement of 12 provided alkaloid 13, which was reduced with LiAlH4 to obtain a mixture of secondary alcohols, 14a,b.Treatment of each of these alcohols with HCl in methanol afforded (-)-alloaristoteline (4).
Indolisation of cyclohexanone phenylhydrazones using phosphorous trichloride
Chakrabarty, Manas,Batabyal, Archana
, p. 199 - 201 (2007/10/02)
Fischer-type indolisation of phenylhydrazones (either preformed of formed in situ) of cyclohexanone and 4-, 3- and 2-methylcyclohexanones in the presence of PCl3 as a cyclising agent furnishes 1,2,3,4-tetrahydro-9H-carbazole, its 3- and 2-methyl derivatives and 11-methyltetrahydrocarbazolenine, respectively in high yields.
