1346005-05-7Relevant 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
supporting information, p. 2175 - 2188 (2015/04/14)
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.
Bronsted acid assisted activation of imide carbonyl group: Regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine
Selvakumar, Jayaraman,Ramanathan, Chinnasamy Ramaraj
supporting information; experimental part, p. 7643 - 7646 (2011/12/03)
Activation of imide carbonyl group with trifluoromethanesulfonic acid facilitates the intramolecular cyclization of phenethylphthalimides to give a fused isoindoloisoquinolinone skeleton. The first one pot regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine has been successfully executed using this methodology.
