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Synfacts 2010(8): 0932-0932
DOI: 10.1055/s-0030-1257762
DOI: 10.1055/s-0030-1257762
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthetic Equivalents for the Preparation of 1,2,3,4-Tetrahydroisoquinolines
H. Kommidi, S. Balasubramaniam, I. S. Aidhen*
Indian Institute of Technology Madras, Chennai, India
Further Information
Publication History
Publication Date:
22 July 2010 (online)
Significance
New synthetic equivalents based on Weinreb amides were developed for a convenient synthesis of various tetrahydroisoquinolines. Two straightforward reactions - N-benzylation and addition of an arylmagnesium halide to the Weinreb amide functionality - afforded the key intermediate for a short synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolines through reduction and an acid-promoted Friedel-Crafts-type cyclization.