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

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.

DOI

10.3906/kim-1310-30

Keywords

Isoindole, norcantharimide, singlet oxygen, ketene, epoxidation

First Page

629

Last Page

637

Recommended Citation

TAN, AYŞE; KAZANCIOĞLU, MUSTAFA ZAHRİTTİN; AKTAŞ, DERYA; GÜNDOĞDU, ÖZLEM; ŞAHİN, ERTAN; KİSHALI, NURHAN; and KARA, YUNUS (2014) "Convenient synthesis of new polysubstituted isoindole-1,3-dione analogues," Turkish Journal of Chemistry: Vol. 38: No. 4, Article 12. https://doi.org/10.3906/kim-1310-30
Available at: https://journals.tubitak.gov.tr/chem/vol38/iss4/12