1970•Canadian Journal of ChemistryOpen access

Cycloaddition reactions. Addition of dimethyl acetylenedicarboxylate to 1-dimethylaminoindene

Terrence William Doyle

Abstract

The cycloaddition of 1-dimethylaminoindene (2) to dimethyl acetylenedicarboxylate to form a fused cyclobutene system 3 is discussed. Compound 3 underwent two modes of ring opening to yield either the indene–maleate system 4 or the benzocycloheptatriene system 5 depending on reaction conditions. The synthesis of a number of multifunctional benzotropones from 5 is discussed.

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Key concepts: Dimethyl acetylenedicarboxylate, Cycloaddition, Cyclobutene, Chemistry, Indene, Yield (engineering), Ring (chemistry), Medicinal chemistry