A Versatile Cyclodehydration Reaction for the Synthesis of Isoquinoline and β-Carboline Derivatives
Mohammad Movassaghi* and Matthew D. Hill
*Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, Email: movassagmit.edu
M. Movassaghi, M. D. Hill, Org. Lett., 2008, 10, 3485-3488.
DOI: 10.1021/ol801264u (free Supporting Information)
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The direct conversion of various amides to isoquinoline and β-carboline derivatives via mild electrophilic amide activation, with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine followed by cyclodehydration upon warming provides the desired products with short overall reaction times.
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Electrophilic activation of N-alkylamides may lead to a transient highly electrophilic nitrilium ion (or pyridinium adduct) that is trapped by the arene ring
M. Movassaghi, M. D. Hill, O. K. Ahmad, J. Am. Chem. Soc., 2007, 129, 10096-10097.
M. Movassaghi, M. D. Hill, J. Am. Chem. Soc., 2006, 128, 14254-14255.