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Synthesis and Identification of Epoxy Derivatives of 5-Methylhexahydroisoindole-1,3-dione and Biological Evaluation by Torrent, Kariny B. A. (author);Alvarenga, Elson S. (author) is a Chemistry article available to read on EtoBox.

What is Synthesis and Identification of Epoxy Derivatives of 5-Methylhexahydroisoindole-1,3-dione and Biological Evaluation about?

Cyclic imides belong to a well-known class of organic compounds with various biological activities, promoting a great interest in compounds with this functional group. Due to the structural complexity of some molecules and their spectra, it is necessary to use several spectrometric methods associated with auxiliary tools, such as the theoretical calculation for the structural elucidation of complex structures. In this work, the synthesis of epoxy derivatives of 5-methylhexahydroisoindole-1,3-diones was carried out in five steps. Diels–Alder reaction of isoprene and maleic anhydride followed by reaction with __m__-anisidine afforded the amide (**2**). Esterification of amide (**2**) with methanol in the presence of sulfuric acid provided the ester (**3**) that cyclized in situ to give imides **4** and **4-ent**. Epoxidation of **4** and **4-ent** with __meta__-chloroperbenzoic acid (MCPBA) afforded **5a** and **5b**. The diastereomers were separated by silica gel flash column chromatography, and their structures were determined by analyses of the spectrometric methods. Their structures were confirmed by matching the calculated ^1^H and ^13^C NMR chemical shifts of (**5a** and **5b**

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Author

Torrent, Kariny B. A. (author);Alvarenga, Elson S. (author)

Publisher

MDPI AG

Published

2021

Language

EN

Field

Chemistry (Life Sciences)