145313-93-5Relevant academic research and scientific papers
Protoberberines from Reissert compounds, II: A new synthesis of 8-methyldibenzo[a,g]quinolizidines
Reimann,Renz
, p. 253 - 258 (2007/10/02)
The Reissert compounds 16 are benzylated by 2-bromomethylacetophenone dioxolane 14 to give the dihydroisoquinolines 5. Treatment of 5 with KOH yields the 1-benzylisoquinolines 6 which spontaneously form the deoxygenated coralynes 4 in acidic solution. 4a
Synthesis of Dibenzoquinolizines - A New Entry to Protoberberines
Reimann, Eberhard,Benend, Helmut
, p. 939 - 948 (2007/10/02)
A novel synthesis to prepare dibenzo-8-quinolizinones 8 is reported using the intramolecular cyclisation of the benzylated Reissert compounds 6 for the key step.Methylation of 8 by methyllithium gives partial deoxygenated coralynes 10 which in turn can be reduced by NaBH4 yielding the 8-methyltetrahydro-protoberberines 11.The structures are assigned by NMR-spectroscopy. Keywords.Reissert compounds; Intramolecular cyclisation; Dibenzo-8-quinolizinones; Deoxygenated coralynes; 8-Methyltetrahydro-protoberberines.
