Copper triflate catalyzed regioselective alkylation of pyrrole: Conversion of 2-alkylated pyrroles to novel pyrrolizine derivatives by self-cyclization

ÜNALEROĞLU C., Aytac S., TEMELLİ B.

HETEROCYCLES, cilt.71, sa.11, ss.2427-2440, 2007 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 71 Sayı: 11
  • Basım Tarihi: 2007
  • Doi Numarası: 10.3987/com-07-11137
  • Dergi Adı: HETEROCYCLES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2427-2440
  • Hacettepe Üniversitesi Adresli: Evet

Özet

Metal triflate catalyzed addition reaction of pyrrole to methyl 2-oxo-4-phenylbut-3-enoate and substituted derivatives generated the related novel alkylated pyrroles regioselectively at C(2) of pyrrole. Among the studied metal triflates, Cu(OTf)(2) was found to be more effective in the addition reaction. The synthesized methyl 2-oxo-4-phenyl-4-(1H-pyrrole-2-yl)butanoate esters underwent self-cyclization by heating and yielded the corresponding methyl 3-hydroxy-1-phenyl-2,3-dihydro-1H-pyrrolizine-3-carboxylate and substituted derivatives. This reaction procedure allowed easy access to pyrrolizine structure in mild reaction conditions.