- Oxidative Pictet-Spengler cyclisations through acceptorless iridium-catalysed dehydrogenation of tertiary amines
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The valuable tetrahydro-β- and γ-carboline skeleta can be accessed through Pictet-Spengler cyclisation initiated by acceptorless dehydrogenation of saturated cyclic amines. The substrate scope for the β-isomers is found to be somewhat limited, but access
- Cooksey, John P.,Saidi, Ourida,Williams, Jonathan M.J.,Blacker, A. John,Marsden, Stephen P.
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- Synthesis of pharmacologically relevant indoles with amine side chains via tandem hydroformylation/fischer indole synthesis
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The sequence of hydroformylation and Fischer indole synthesis starting from amino olefins and aryl hydrazines is described. In a convergent manner, the two units bearing pharmacologically relevant substituents are assembled in the final indolization step. This modular and diversity-oriented approach to tryptamines and homotryptamines can be conducted in water and allows synthesis of branched and nonbranched tryptamines as well as tryptamine-based pharmaceuticals such as the 5-HT1D agonist L 775 606.
- Schmidt, Axel M.,Eilbracht, Peter
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p. 5528 - 5535
(2007/10/03)
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- N-Alkylation of phenethylamine and tryptamine
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A clean and efficient method for the N-alkylation of tryptamine and phenethylamine, employing alcohols as the alkylating agents, has been developed. The reaction proceeds via catalytic electronic activation, involving an iridium catalyst which activates the alcohol by borrowing hydrogen from the substrate, returning it later in the catalytic cycle. Some examples of N-heterocyclisation have been performed employing a diol as the substrate.
- Cami-Kobeci, Gerta,Slatford, Paul A.,Whittlesey, Michael K.,Williams, Jonathan M.J.
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p. 535 - 537
(2007/10/03)
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- STEREOREGULATION OF THE C(12b)H-C(2)H RELATIONSHIP IN THE PREPARATION OF 2-SUBSTITUTED 1,2,3,4,6,7,12,12b-OCTAHYDROINDOLOQUINOLIZINES
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Stereochemical control in the preparation of 2-substituted 1,2,3,4,6,7,12,12b-octahydroindoloquinolizines possessing at will the C(12b)H-C(2H) cis or trans configuration was achieved by catalytic reduction of the 2,3-dehydro analoques, which were either unsubstituted on the indole nitrogen or substituted with a BOC-group, respectively.The contribution of different conformations to the conformational equilibrium of the prepared compounds was estimated by 13C NMR spectral analysis.
- Lounasmaa, Mauri,Jokela, Reija
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p. 3975 - 3992
(2007/10/02)
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- RUTHENIUM CATALYZED SYNTHESIS OF TERTIARY AMINES FROM AMINES AND ALCOHOLS
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Unsymmetrical secondary and tertiary amines are prepared by the ruthenium catalyzed reaction of alcohols with amines, which provides highly efficient method for synthesis of cyclic amines.
- Murahashi, Shun-Ichi,Kondo, Kaoru,Hakata, Toshiyuki
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p. 229 - 232
(2007/10/02)
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