Tetrahedron

36-Dimethoxybenzocyclobutenone: a reagent for quinone synthesis

M Azadi-Ardakani, TW Wallace

Index: Azadi-Ardakani, Manouchehr; Wallace, Timothy W. Tetrahedron, 1988 , vol. 44, # 18 p. 5939 - 5952

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Citation Number: 38

Abstract

3, 6-Dimethoxybenzocyclobutenone 4 is prepared in four efficient steps from 2, 5- dimethoxybenzoic acid 8. The derived benzocyclobutenol 13 undergoes electrocyclic ring opening at 110–115° C to give the hydroxy-o-quinone dimethide 21, which reacts with dienophiles to give 5, 8-dimethoxy-1, 2, 3, 4-tetrahydro-1-naphthol derivadves stereoselecdvely. Since the ketone 4 can be functionalised at C-5 using electrophiles and ...

~37%

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~85%

~99%

~99%

~72%

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