75397-67-0Relevant academic research and scientific papers
Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- And 7-membered C-ring homologues
Kurouchi, Hiroaki
, p. 653 - 658 (2021/02/06)
A route to the direct amidation of aromatic-ring-tetheredN-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.
Synthesis and Photo-oxygenation of Some Substituted 1-Benzyl-3,4-dihydroisoquinolines. Mechanism of Enamine Photo-oxygenation
Martin, Ned H.,Jefford, Charles W.
, p. 762 - 774 (2007/10/02)
The synthesis of a series of substituted 1-benzyl-3,4-dihydroisoquinolines by Bischler-Napieralski cyclization is described.Competitive methylene blue sensitized photo-oxygenation experiments allowed the determination of relative rates of photo-oxygenation of 1-benzyl-3,4-dihydroisoquinolines.Substituents were shown to affect both the equilibrium concentration of the tautomeric enamine and the overall photo-oxygenation rate.After correcting for differences in enamine concentration, the relative rate data provided a diagnostic probe of the reaction mechanism, which involves transfer of charge in the rate-limiting step.
REGIOPSPECIFIC OXIDATION OF SUBSTITUTED 1-BENZYL-3,4-DIHYDROISOQUINOLINES USING SINGLET OXYGEN
Martin, Ned H.,Champion, Sidney L.,Belt, Phillip B.
, p. 2613 - 2616 (2007/10/02)
Singlet oxygen regiospecifically oxidizes 1-benzyl-3,4-dihydroisoquinoline to 1-benzoyl-3,4-dihydroisoquinoline.Mechanistic studies do not distinguish between a dioxetane or the alternative zwitterionic peroxide intermediate.
