Convenient synthesis of new polysubstituted isoindole-1,3-dione analogues

Authors : Ayşe TAN, Mustafa Zahrittin KAZANCIOĞLU, Derya AKTAŞ, Özlem GÜNDOĞDU, Ertan ŞAHİN, Nurhan HORASAN KİSHALI, Yunus KARA

Pages : 629-637

Doi:10.3906/kim-1310-30

View : 16 | Download : 10

Publication Date : 0000-00-00

Article Type : Research Paper

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