335157-46-5Relevant academic research and scientific papers
Synthesis of condensed tetrahydroisoquinoline class of alkaloids by employing TfOH-mediated imide carbonyl activation
Selvakumar, Jayaraman,Rao, Ramana Sreenivasa,Srinivasapriyan, Vijayan,Marutheeswaran, Srinivasan,Ramanathan, Chinnasamy Ramaraj
, p. 2175 - 2188 (2015)
Isoquinoline-based polycyclic lactams such as isoindoloisoquinolinones, pyrroloisoquinolinones, and benzo[a]quinolizinones were successfully assembled from the corresponding imides by using a TfOH-mediated (TfOH = trifluoromethanesulfonic acid) imide carbonyl activation and cyclization strategy. By employing this simple method, the isoquinoline alkaloids crispine A, trolline/oleracein E, and erythrinarbine were successfully synthesized in racemic form. The reaction of unsymmetrical N-phenethylphthalimides with TfOH displayed excellent regioselectivity, which was rationalized by DFT calculations.
An unusual reactivity of BBr3: Accessing tetrahydroisoquinoline units from N-phenethylimides
Selvakumar, Jayaraman,Makriyannis, Alexandros,Ramanathan, Chinnasamy Ramaraj
supporting information; experimental part, p. 4056 - 4058 (2010/10/21)
Isoindoloisoquinalinone, pyrroloisoquinolinone and benzo[a]quinolizinone units are constructed via intramolecular cyclization of the methoxy substituted N-phenethylimides using BBr3.
