Synthesis of substituted 1, 2-dihydroisoquinolines by the intramolecular 1, 3-dipolar alkyl azide-olefin cycloaddition

JM Liu, JJ Young, YJ Li, CK Sha

Index: Liu, Jia-Ming; Young, Jenn-Jong; Li, Yu-Jang; Sha, Chin-Kang Journal of Organic Chemistry, 1986 , vol. 51, # 7 p. 1120 - 1123

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Citation Number: 38

Abstract

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 ...