53629-44-0Relevant academic research and scientific papers
Synthesis of 8-oxoberbines and related benzolactams by Pd(OAc) 2-catalyzed direct aromatic carbonylation
Miyazawa, Mamoru,Tokuhashi, Takashi,Horibata, Akiyoshi,Nakamura, Takatoshi,Onozaki, Yu,Kurono, Nobuhito,Senboku, Hisanori,Tokuda, Masao,Ohkuma, Takeshi,Orito, Kazuhiko
, p. E48-E54 (2013)
A variety of alkoxy-substituted benzolactams with a berbine or yohimbane skeleton were prepared from 1-benzyl-1,2,3,4-tetrahydroisoquinolines or 1-benzyl-1,2,3,4-tetrahydro-β-carbolines by a phosphine-free Pd(II)-catalyzed direct aromatic carbonylation in a Pd(OAc)2-Cu(OAc) 2 catalytic system. The site selectivity was compared with that of the carbonylation with Pd(OAc)2 or Pd(OAc)2·2 PPh3, respectively.
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.
