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Note | Regular issue | Vol 63, No. 2, 2004, pp.401-409
Published online, 15th December, 2003
DOI: 10.3987/COM-03-9936
Alkali Metal-mediated Synthesis of 1- and 4-Substituted N-Alkyl-1,2,3,4-tetrahydroisoquinolines

Ugo Azzena,* Luisa Pisano, and Mario Pittalis

*Department of Chemistry, University of Sassari, Via Vienna 2, I-07100 Sassari, Italy

Abstract

Reductive cleavage by electron transfer from Li or K metal of 1-alkoxy-substituted N-alkyltetrahydroisoquinolines led to the formation of organometallic derivatives. Quenching of these intermediates with electrophilic reagents afforded 1- or 4-substituted N-alkyl-1,2,3,4-tetrahydroisoquinolines, depending upon the nature of the metal.