A Golden Synthetic Approach for 2(1H-pyrrole-1yl)-aniline and pyrrolo[1,2-a]quinoxaline Through Gold-carbene Intermediate

Taşdemir V., Genç H., Menges N.

Synlett, cilt.35, sa.7, ss.801-806, 2022 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 35 Sayı: 7
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1055/a-2159-9400
  • Dergi Adı: Synlett
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica
  • Sayfa Sayıları: ss.801-806
  • Anahtar Kelimeler: cyclization, diaminoarenes, gold catalysis, oxidation, pyrroloquinoxalines, pyrrolylanilines
  • Van Yüzüncü Yıl Üniversitesi Adresli: Evet

Özet

The pyrrolo[1,2-a]quinoxaline skeleton has significant potential for many biological and optical applications. Hence, in this study, unconjugated ynone derivatives are reacted with 1,2-diaminoarenes under gold-catalyzed cyclization. The reaction gives 2(1H-pyrrole-1yl)-aniline, which is a valuable starting material, and Pyrrolo[1,2-a]quinoxaline through a one-pot and single-step approach. A reaction mechanism for the formation of the pyrrolo[1,2-a]quinoxaline skeleton featuring a key gold-carbene intermediate is proposed. On the other hand, the methyl group on the C-2 position of 2(1H-pyrrole-1yl)-anilines is oxidized with SeO2, resulting in a pyrrolo[1,2-a]quinoxaline skeleton, which gives 14 different pyrrolo[1,2-a]quinoxaline derivatives.