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Publication Type : Journal Article
Publisher : Eur. J. Org. Chem
Source : Eur. J. Org. Chem. 10, (2015) 2175
Url : https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201403617
Campus : Mysuru
Department : Chemistry
Year : 2015
Abstract : 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.
Cite this Research Publication : J. Selvakumar, R. S. Rao, V. Srinivasapriyan, S. Marutheeswaran, C. R. Ramanathan “Synthesis of condensed tetrahydroisoquinoline class of alkaloids employing TfOH mediated imide carbonyl activation.” Eur. J. Org. Chem. 10, (2015) 2175