Synthesis of spiroindolenine-cyclopentenedione skeletons and their chemical behaviours: the first example of a lactone-type spiroindolenine structure


Tan Uygun M., Mengeş N.

ORGANIC & BIOMOLECULAR CHEMISTRY, vol.20, no.20, pp.4161-4166, 2022 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 20 Issue: 20
  • Publication Date: 2022
  • Doi Number: 10.1039/d2ob00396a
  • Journal Name: ORGANIC & BIOMOLECULAR CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Chimica, Compendex, EMBASE, MEDLINE, Veterinary Science Database
  • Page Numbers: pp.4161-4166
  • Van Yüzüncü Yıl University Affiliated: Yes

Abstract

A manageable, one-pot, and high-yield protocol for synthesising highly reactive spiroindolenine derivatives is reported. Spiroindolenines are furnished by a reaction between DCC (dicyclohexylcarbodiimide) and indole-3-butenoic acid derivatives. The protocol proposed here involves the construction of a carbon-carbon bond through intramolecular domino cyclisation. The reaction mechanism for spirocyclisation is discussed; both NMR and X-ray analysis were used to verify the structure of spiroindolenine. The applied strategy allowed the formation of spiroindolenine with a dione substructure, which is an unknown compound with a spirocyclic nucleus. Further reactions of spiroindolenines with di-amines, a primary amine, and alcohol have been reported, and new types of indole derivatives, such as indoloquinoxalines, where the spirocentre atom undergoes a nucleophilic attack, are yielded.