Journal of Organic Chemistry p. 1120 - 1123 (1986)
Update date:2022-08-02
Topics:
Liu, Jia-Ming
Young, Jenn-Jong
Li, Yu-Jang
Sha, Chin-Kang
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.
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