Authors: AYŞE TAN, MUSTAFA ZAHRİTTİN KAZANCIOĞLU, DERYA AKTAŞ, ÖZLEM GÜNDOĞDU, ERTAN ŞAHİN, NURHAN KİSHALI, YUNUS KARA
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 OsO_4, 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
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