Title of article
Convenient synthesis of new polysubstituted isoindole-1,3-dione analogues
Author/Authors
TAN, Ayşe Atatürk University - Faculty of Sciences - Department of Chemistry, Turkey , KAZANCIOĞLU, Mustafa Zahrittin Atatürk University - Faculty of Sciences - Department of Chemistry, Turkey , AKTAŞ, Derya Atatürk University - Faculty of Sciences - Department of Chemistry, Turkey , GÜNDOĞDU, Özlem Atatürk University - Faculty of Sciences - Department of Chemistry, Turkey , ŞAHİN, Ertan Atatürk University - Faculty of Sciences - Department of Chemistry, Turkey , HORASAN KİSHALI, Nurhan Atatürk University - Faculty of Sciences - Department of Chemistry, Turkey , KARA, Yunus Atatürk University - Faculty of Sciences - Department of Chemistry, Turkey
From page
629
To page
637
Abstract
Three new polysubstituted isoindole-1,3-diones were prepared from 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydro-isoindole-1,3-dione. The reaction of 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydro-isoindole-1,3-dione with m-CPBA gave the corresponding epoxide. The triacetate derivative was obtained via cis-hydroxylation using OsO4, followed by acetylation. An aromatic derivative, a secondary reaction product, was also formed during the acetylation. Finally, a tricyclic derivative from 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydro-isoindole-1,3-dione was synthesized via dichloroketene addition under microwave irradiation. The exact structures of epoxide and tricyclic derivatives were determined by X-ray diffraction analysis.
Keywords
Isoindole , norcantharimide , singlet oxygen , ketene , epoxidation
Journal title
Turkish Journal of Chemistry
Journal title
Turkish Journal of Chemistry
Record number
2533366
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