59414-58-3Relevant academic research and scientific papers
A NEW SYNTHESIS OF THE PROTOBERBERINE SYSTEM
Marsden, Richard,MacLean, David B.
, p. 2063 - 2066 (1983)
The reaction of phthalide anions with 3,4-dihydroisoquinolines yields 13-hydroxy-8-oxotetrahydroprotoberberines with the hydrogen atoms at C-13 and C-14 trans to one another; reduction of the lactams yields the corresponding 13-hydroxytetrahydroprotoberberines.
BENZOPHENANTHRIDINES. VI. TRANSFORMATIONS OF PROTOBERBERINE ALKALOIDS INTO BENZOPHENANTHRIDINE ALKALOIDS. HOFMANN DEGRADATION OF α-N- AND β-N-METHYL-(+/-)-13α-HYDROXYXYLOPININE IODIDES
Sladkov, V. I.,Sazonova, N. M.,Kuleshova, L. N.,Lindeman, S. V.,Struchkov, Yu. T.,Suvorov, N. N.
, p. 767 - 773 (2007/10/02)
(+/-)-13α-Hydroxyxylopinine was synthesized from 3,4-dihydropapaverine dichlorophosphate through a stage involving the formation of 3,4-dihydropapaveraldine and α-hydroxynorlaudanosine.The product was converted by the action of methyl iodide in ethanol in
Condensation of cyclic and acyclic imines with phthalide anions. Synthesis of protoberberines and substituted 3,4-dihydro-2-methyl-1(2H)-isoquinolones
Marsden, Richard,MacLean, David B.
, p. 1392 - 1399 (2007/10/02)
3,4-Dihydroisoquinolines react with anions derived from phthalides and 3-methylphthalides in tetrahydrofuran yielding 13-hydroxy-8-oxotetrahydroprotoberberines and 13-hydroxy-13-methyl-8-oxotetrahydroprotoberberines, respectively.Only one of two possible diastereomers is formed.The lactams may be reduced to the corresponding protoberberines with lithium aluminium hydride.The reaction of the acyclic imine, 3,4-dimethoxybenzylidenemethylamine, with anions derived from phthalide, 3-phenylphthalide, and 5,6-dimethoxyphthalide, has been investigated.In all cases separable mixtures of diastereomeric substituted 3,4-dihydro-1(2H)-isoquinolones were formed.
