Turkish Journal of Chemistry
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.
DOI
10.3906/kim-1310-30
Keywords
Isoindole, norcantharimide, singlet oxygen, ketene, epoxidation
First Page
629
Last Page
637
Recommended Citation
TAN, A, KAZANCIOĞLU, M. Z, AKTAŞ, D, GÜNDOĞDU, Ö, ŞAHİN, E, KİSHALI, N, & KARA, Y (2014). Convenient synthesis of new polysubstituted isoindole-1,3-dione analogues. Turkish Journal of Chemistry 38 (4): 629-637. https://doi.org/10.3906/kim-1310-30
