Modular one-pot synthesis of tetrasubstituted pyrroles from alpha-(alkylideneamino)nitriles.
2,3,4,5-Tetrasubstituted pyrroles have been prepared with high regioselectivity by a formal cycloaddition of alpha-(alkylideneamino)nitriles and nitroolefins followed by elimination of HCN and HNO2. The reaction allows the convergent construction of the pyrrole ring in four steps from a nitroalkane and three aldehydes.
Bergner
Ines
I
Institute of Organic Chemistry, University of Mainz, Duesbergweg 10-14, D-55128 Mainz, Germany.
Opatz
Till
T
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D003500:Cyclization; D009570:Nitriles / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis*
D000447:Aldehydes; D000475:Alkenes; D009570:Nitriles; D009574:Nitro Compounds; D011758:Pyrroles