Synthesis of Substituted 1,2-Dihydroisoquinolines by the Intramolecular 1,3-Dipolar Alkyl Azide-Olefin Cycloaddition

Article abstract of DOI:10.1021/jo00357a034

A general synthesis of substituted 1,2-dihydroisoquinolines based on intramolecular 1,3-dipolar cycloaddition of alkyl azides and olefins is described.Reaction of bromide 4 with sodium azide afforded azide 5, which underwent 1,3-dipolar cycloaddition intramolecularly to give triazoline 6 .Rearrangement of triazoline 6 on silica gel gave diazo compound 7.Treatment of 7 with rhodium acetate afforded substituted 1,2-dihydroisoquinoline 9 in good overall yield.