One-pot synthesis of 4,5,6-triacetoxyisoindole-1,3‑dione derivatives by hydride transferring agent in Ac2O: Explanation of the regioselectivity in the molecule by theoretical calculations

Gundogdu O., Atalay A., ŞAHİN E., KARA Y.

Journal of Molecular Structure, cilt.1314, 2024 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1314
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1016/j.molstruc.2024.138767
  • Dergi Adı: Journal of Molecular Structure
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Anahtar Kelimeler: Epoxy alcohol, Hydride transfer, Isoindole-1,3‑dione, Regioselectivity, Ring opening reaction
  • Atatürk Üniversitesi Adresli: Evet

Özet

Isoindole-1,3‑dione derivatives containing an epoxy alcohol unit were synthesized. Epoxy alcohols were converted to the corresponding 1,2,3-triacetate derivatives in a one-pot manner using the NaBH4/Ac20 system for the first time and in high yield. C-3 selective ring-opening products were obtained with good yield and with stereospecificity with the NaBH4/Ac2O system at 139–140 °C. The exact configuration of 2-methyl-1,3-dioxooctahydro-1H-isoindole-4,5,6-triyltriacetate was determined by X-ray diffraction analysis which was obtained from the reaction of epoxy alcohol by hydride transferring agent in acetic anhydride. On the other hand, theoretical computations were carried out to explain the regioselectivity in the ring opening reaction of epoxy alcohols. The results showed that the ring-opening reaction of epoxy alcohol proceeds in a thermodynamically controlled manner and regioselectivity occurs depending on the stability of the products.