ABSTRACT
The title reaction provides a direct entry to a range of biologically relevant annulated pyrroles via a domino process involving a regioselective one-carbon homologation of cyclic ketones as the key step.
Subject(s)
Cyanides/chemistry , Pyrroles/chemical synthesis , Cyclization , Ketones/chemistry , Molecular Structure , Pyrroles/chemistry , StereoisomerismABSTRACT
A pentiptycene-derived p-phenylenediamine mimics a molecular double-rotor system that displays redox-dependent rotation rates for the amino rotors about the pentiptycene-amine C-N bond. The rotation is accelerated in the radical cation state but stopped in the di(radical cation) state. Electronic interplay of the two rotors is also discussed.
ABSTRACT
4-Bis(methylthio)methylene-2-phenyloxazol-5-one has been shown to be a versatile template for the synthesis of various 2-phenyl-3,4-substituted oxazoles via nucleophilic ring-opening of oxazolone with various oxygen, nitrogen, and carbon nucleophiles and subsequent 5-endo cyclization of the resulting acyclic adducts in the presence of silver carbonate.