Synthesis of Indolizines by Dimerization of N-Propargylated Pyrroles via Allene Intermediates

Kuzu B. , Gül S., Tan M. , Mengeş N. , Balci M.

ChemistrySelect, cilt.6, sa.9, ss.2366-2372, 2021 (SCI Expanded İndekslerine Giren Dergi) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 6 Konu: 9
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1002/slct.202100045
  • Dergi Adı: ChemistrySelect
  • Sayfa Sayıları: ss.2366-2372


© 2021 Wiley-VCH GmbHTen different N-propargyl pyrrole derivatives having various substituents at the C-2 position were synthesized. These derivatives were converted into indolizine derivatives by the [2+2] cycloaddition reaction of pyrrole N-allene, forming in situ, by heating in PrOH in basic medium. The structures were characterized by NMR and X-ray crystallography. The N-propargylated derivatives smoothly underwent intermolecular cyclizations to produce indolizine derivatives in good yields. We proposed a radical mechanism for the dimerization. Reaction of an allene product with butylated hydroxytoluene (BHT), a radical scavenger, did not give any dimerization product. This result supports the radical reaction.