Synthesis of new hexahydro-1H-isoindole-1,3(2H)-dione derivatives from 2-ethyl/pheny1-3a,4,7,7a-tetrahydro-1H-isoindole-1,3-(2H)-dione

Tan A., KOÇ B., KİSHALI N., ŞAHİN E., KARA Y.

TURKISH JOURNAL OF CHEMISTRY, cilt.40, sa.5, ss.830-840, 2016 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 40 Sayı: 5
  • Basım Tarihi: 2016
  • Doi Numarası: 10.3906/kim-1511-66
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.830-840
  • Anahtar Kelimeler: Norcantharimide, cis-hydroxylation, epoxidation, ring opening epoxide, reduction of azide, NORCANTHARIDIN ANALOGS, CONVENIENT SYNTHESIS, ANTICANCER ACTIVITY, CARCINOMA-CELLS, PROTEIN, PHOSPHATASE-2A, CYCLOADDITION
  • Atatürk Üniversitesi Adresli: Evet

Özet

A new and appropriate synthesis for hexahydro-1H-isoindole-1,3(2H)-dione derivatives has been developed starting from 3-sulfolene. The epoxidation of 2-ethyl/pheny1-3a,4,7,7a-tetrahydro-1H-isoindole-1,3-(2H)-dione and then the opening of the epoxide with nucleophiles gave hexahydro-1H-isoindole-1,3(2H)-dione derivatives. Amino and triazole derivatives of hexahydro-1H-isoindole-1,3(2H)-dione were synthesized from the formed product by the opening reaction of the epoxide with sodium azide. Hydroxyl analogues were obtained from cis-hydroxylation of 2-ethyl/pheny1-3a,4,7,7atetrahydro-1H-isoindole-1,3-(2H)-dione. The hydroxyl groups were converted to acetate.