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

TAN A., KAZANCIOĞLU M. Z., Aktas D., GÜNDOĞDU O., ŞAHİN E., Kishali N., ...Daha Fazla

TURKISH JOURNAL OF CHEMISTRY, cilt.38, sa.4, ss.629-637, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 38 Sayı: 4
  • Basım Tarihi: 2014
  • Doi Numarası: 10.3906/kim-1310-30
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.629-637
  • Anahtar Kelimeler: Isoindole, norcantharimide, singlet oxygen, ketene, epoxidation, CANTHARIDIN ANALOGS, CARCINOMA-CELLS, DERIVATIVES
  • Atatürk Üniversitesi Adresli: Evet

Özet

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.