24997-88-4Relevant articles and documents
Trapping of iminiums by the indole nucleus during catalytic hydrogenation of nitriles: A rapid synthesis of tetrahydro-β-carbolines
Diker, Khalid
, p. 2497 - 2500 (2007/10/02)
Reductive self-condensation of indole acetonitrile upon catalytic hydrogenation over Pd·C in acetic acid yielded 1-(3-indolylmethyl)-1,2,3,4-tetrahydro-β-carboline. Hydrogenating 3,4-dimethoxyphenylacetonitrile failed to give tetrahydropapaverine, but a cross reaction between indole acetonitrile and 3,4-dimethoxyphenylacetonitrile allowed isolation of 1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydro-β-carboline, which was otherwise prepared (76%) by catalytic hydrogenation of a mixture of tryptamine and 3,4-dimethoxyphenylacetonitrile. Besides an easy access to the yohimbane skeleton, the reaction opens the way to a useful general synthesis of tetrahydro-β-carbolines.
Studies on the syntheses of heterocyclic compounds. CCXII. By-product in the prepatation of homoveratrylamine by catalytic hydrogenation of 3,4-dimethoxybenzyl cyanide and its derivation to 2-phenethylisoquinoline derivatives
Kametani,Ogasawara,Harada
, p. 163 - 165 (2007/10/05)
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