4468-58-0Relevant articles and documents
The palladium-catalyzed preparation of condensed tetracyclic heterocycles and their application to the synthesis of rac-mangochinine
Vincze, Zoltan,Biro, A. Beatrix,Csekei, Marton,Timari, Geza,Kotschy, Andras
, p. 1375 - 1385 (2007/10/03)
Dihydroisoquinoline derivatives and their analogues, prepared by the Bischler-Napieralsky reaction, were converted to their indole-fused derivatives. Scope and limitations of the palladium-catalyzed reaction, proceeding through the tautomeric enamine forms of these compounds, were studied and the process was extended to the preparation of racemic mangochinine. Georg Thieme Verlag Stuttgart.
Photochemical synthesis of 7,8-dioxygenated isoquinoline alkaloids
Suau, Rafael,Valpuesta, Maria,Torres, Gregorio
, p. 1315 - 1318 (2007/10/02)
A new approach to the synthesis of 7,8-dioxygenated tetrahydroisoquinoline alkaloids based on the photo-Fries rearrangement of esters derived from 3-hydroxy-4-methoxy phenylacetonitrile is reported. The procedure was applied to the synthesis of the alkaloid Arizonine and 1-benzyl tetrahydroisoquinoline precursor of cularine and 1,2-berbine alkaloids.
Oxidation of Methoxy- and/or Methyl-Substituted Benzenes and Naphthalenes to Quinones and Phenols by H2O2 in HCOOH
Orita, Hideo,Shimizu, Masao,Hayakawa, Takashi,Takehira, Katsuomi
, p. 1652 - 1657 (2007/10/02)
The oxidation of a number of arenes (methoxybenzenes, methylbenzenes, and naphthalenes) to quinones and phenols by H2O2 in HCOOH has been examined.Methoxybenzenes were much more easily oxidized to p-benzoquinones than methylbenzenes (e.g., 1,3,5-trimethoxybenzene was oxidized to 2,6-dimethoxy-p-benzoquinone in a 75percent yield and 1,2,4-trimethylbenzene to 2,3,5-trimethyl-p-benzoquinone in a 16percent yield).Electron-withdrawing substituents, such as nitro, cyano, and chloro groups, lowered the conversion of reactants and changed the product selectivity from quinones to phenols.Methoxybenzonitriles were oxidized to corresponding phenols in a moder ate yield (e.g., 2,6-dimethoxybenzonitrile to 3-hydroxy-2,6-dimethoxybenzonitrile in a 39percent yield and a 64percent selectivity).