Access to pyrrole-based heterocyclic compounds via addition of pyrrole to C=C and C=N bonds

ÜNALEROĞLU C., TEMELLİ B., Tasgin D. I.

PURE AND APPLIED CHEMISTRY, cilt.86, sa.6, ss.925-932, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 86 Sayı: 6
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1515/pac-2013-1109
  • Dergi Adı: PURE AND APPLIED CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.925-932
  • Hacettepe Üniversitesi Adresli: Evet

Özet

A series of metal triflate-catalyzed addition reactions of pyrrole to C=C and C=N bonds have been investigated to access pyrrole-based heterocyclic compounds. The addition of pyrrole to different alpha,beta-unsaturated compounds or N-tosyl imines afforded suitable structures for the construction of [5-5] bicyclic systems or porphyrins, respectively. Intramolecular cyclization reactions were applied for the synthesis of pyrrolizine derivatives. In the other reaction mode, intermolecular cyclization reactions gave A(4)- and trans-A(2)B(2)-meso-substituted porphyrins under mild reaction conditions with low scrambling.