InCl3-Catalyzed One-Pot Synthesis of Pyrrolo/Indolo- and Benzooxazepino-Fused Quinoxalines

Aksakal N. E., ZORA M.

ACS Omega, cilt.9, sa.30, ss.33251-33260, 2024 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 9 Sayı: 30
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1021/acsomega.4c05239
  • Dergi Adı: ACS Omega
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Directory of Open Access Journals
  • Sayfa Sayıları: ss.33251-33260
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

In this paper, we describe an efficient InCl3-catalyzed two-component reaction of 1-(2-aminophenyl)pyrroles/indoles and 2-propargyloxybenzaldehydes for the direct synthesis of 12bH-benzo[6,7]1,4-oxazepino[4,5-a]pyrrolo/indolo[2,1-c]quinoxalines. This high atom- and step-economical one-pot process generates three new C/N-C bonds in a single synthetic operation, resulting in the formation of new six- and seven-membered heterocyclic rings. The easy availability of the starting materials, the use of the relatively inexpensive indium catalyst, and the good substrate scope are the salient features of this strategy. The proposed mechanistic pathway involves imine formation, two consecutive cyclizations via electrophilic aromatic substitution and nucleophilic addition reactions, and the H shift step.