Facile synthesis of unknown 6,7-dihydrofuro[3,4-c]pyridines and 3,4-diaryloylpyridines from N-homopropargylic β-enaminones


YILMAZ E. S., Kaya K., ZORA M.

Organic and Biomolecular Chemistry, cilt.23, sa.9, ss.2133-2141, 2025 (SCI-Expanded, Scopus) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 23 Sayı: 9
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1039/d4ob01884b
  • Dergi Adı: Organic and Biomolecular Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Chimica, Compendex, MEDLINE, Veterinary Science Database
  • Sayfa Sayıları: ss.2133-2141
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

In this paper, we have uncovered a new reaction of N-homopropargylic β-enaminones, i.e. N-(4-phenyl-3-butynyl)-β-enaminones. When subjected to a reaction with excess molecular iodine or N-iodosuccinimide in the presence of cesium carbonate, N-homopropargylic β-enaminones afford 6,7-dihydrofuro[3,4-c]pyridines in low to moderate yields. The generation of two new C/O-C bonds during the reaction leads to the construction of unknown heterobicyclic 5,6-fused ring systems. In some reactions, 3,4-diaryloylpyridines are also observed in low yields. During the formation of 3,4-diaryloylpyridines, a new carbonyl (ketone) group is generated. The synthesized 6,7-dihydrofuro[3,4-c]pyridines and 3,4-diaryloylpyridines may be of use in pharmaceutical and medicinal chemistry as new and novel molecular entities and structural leads.