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

作者：Unaleroglu Canan^*; Temelli Baris; Tasgin Dilek Isik

来源：Pure and Applied Chemistry, 2014, 86(6): 925-932.

DOI：10.1515/pac-2013-1109

• C-C bond formation
• Chemical Synthesis
• dipyrromethane
• heterocyclic chemistry
• IUPAC Congress-44
• metal triflates
• porphyrins
• pyrroles
• pyrrolizines

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.

• 出版日期2014-6