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.
Isoindole, norcantharimide, singlet oxygen, ketene, epoxidation
TAN, AYŞE; KAZANCIOĞLU, MUSTAFA ZAHRİTTİN; AKTAŞ, DERYA; GÜNDOĞDU, ÖZLEM; ŞAHİN, ERTAN; KİSHALI, NURHAN; and KARA, YUNUS
"Convenient synthesis of new polysubstituted isoindole-1,3-dione analogues,"
Turkish Journal of Chemistry: Vol. 38:
4, Article 12.
Available at: https://journals.tubitak.gov.tr/chem/vol38/iss4/12