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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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Abstract

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



Single-Step Synthesis of Pyridine Derivatives

M. Movassaghi, M. D. Hill, O. K. Ahmad, J. Am. Chem. Soc., 2007, 129, 10096-10097.

Single-Step Synthesis of Pyrimidine Derivatives

M. Movassaghi, M. D. Hill, J. Am. Chem. Soc., 2006, 128, 14254-14255.


Key Words

3,4-dihydroisoquinolines, isoquinolines, Bischler-Napieralski Reaction, microwave synthesis


ID: J54-Y2008-1480