Base-promoted Rearrangements of ester groups in 3a,7a-dihydroindole-2,3,3a,4-tetraester

초록

Tetramethyl 3a,7a-dihydro-1-methyl-1H-indole-2,3,3a,4-tetracarboxylate which is an 1:2 adduct of 1-methylpyrrole and dimethyl acetylenedicarboxylate underwent isomerization catalyzed by sodium methoxide to form a 5,7a-dihydro-1-methyl-1H-indole-2,3,4,5-tetracarboxylate, its 5,6-dihydro isomer, and a ring opening product which is an azonine derivative. Fully aromatized esters such as 1-methylindole2,3,4-triester, 1-methylindole-2,3,4,5-tetraester and 1-methyl-2,3,4,6-tetraester were also isolated. An indole compound which could be formed by conjugative addition of the methoxide ion was also isolated.

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