F. El-Samahy
Jan 1, 2005
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Journal
Journal of Chemical Research
Abstract
The reaction of (E)-(2-oxo-1,2-dihydroindol-3-ylidene)acetic acid esters (1) with methyl ethyl ketone in the presence of morpholine as a catalyst gave 4-oxo-2-(2-oxo-2,3-dihydro-1H-indole-3-yl)hexanoic acid esters, a diastereomeric mixture of two isomers (2A and 2B). Using aluminium oxide as a catalyst for the above reaction led to the formation of 4-oxo-3-methyl-2-(2-oxo-2,3-dihydro–1H-indole-3-yl)-pentanoic acid esters as a mixture of three isomers 3A, 3B and 3C, which upon methylation with methyl iodide in acetone and in the presence of anhydrous potassium carbonate yield the corresponding methylated products. The structural assignments of the new compounds are based on their chemical and spectroscopic properties. The stereochemical structures of 5aA, 5bB and 5aC are identified by X-ray analysis.