Synthesis of Pyrrolizinone and Pyrrolizino[1,2-a]pyrrolizin-5-one Skeletons Starting From Pyrrole Through A Single-Step and Catalyst-Free Approach

Amudi K., Kuzu B., Kolak S., Genç H., Mengeş N.

Synlett, cilt.34, sa.11, ss.1265-1269, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 34 Sayı: 11
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1055/a-2006-4390
  • Dergi Adı: Synlett
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, EMBASE
  • Sayfa Sayıları: ss.1265-1269
  • Anahtar Kelimeler: furandiones, alkaloids, Michael addition, decarboxylation, pyrrolizinones, pyrrolizinopyrrolizinones
  • Van Yüzüncü Yıl Üniversitesi Adresli: Evet

Özet

1H-Pyrrole and lactone-type 2,3-furandione derivatives were reacted in anhydrous diethyl ether (Et2O) at room temperature, and then one of the important alkaloid skeletons, pyrrolizinone derivatives, were synthesized via a single step and catalyst-free approach. Various pyrrolizinone derivatives having various substituents such as phenyl, substituted phenyl, thiophene, -CF3, naphthalene, bi-phenyl, ester, and oxalate were yielded. Employing an equimolar pyrrole molecule yielded pyrrolizinones, while using an excess molar of pyrrole yielded pyrrolizino[1,2-a]pyrrolizin-5-one which is not present in the literature. Yield of purified molecules was up to 91%. One of the cyclization processes was carried out on a gram-scale, yielding 0.952 g (71%).