Microwave-assisted, solvent-free synthesis of 1-(alpha- or beta-hydroxynaphthyl)-1,2,3,4-tetrahydroisoquinolines by the Mannich reaction

作者：Szatmari Istvan; Lazar Laszlo; Fulop Ferenc^*

来源：Tetrahedron Letters, 2006, 47(23): 3881-3883.

DOI：10.1016/j.tetlet.2006.03.169

• Mannich reaction
• nucleophilic addition
• dihydroisoquinoline
• 2-naphthol
• 1-naphthol

As a new extension of the Mannich reaction of naphthols, 1-(hydroxynaphthyl)-substituted 1,2,3,4-tetrahydroisoquinolines were synthesized by the nucleophilic addition of 1- or 2-naphthol to 3,4-dihydroisoquinolines under solvent-free conditions, using microwave irradiation. The additions to 3-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline proved to be a highly diastereo-selective processes, resulting in the cis isomers as the main or the only products.

• 出版日期2006-6-5