Discovery and Development of a Class of New Conversion (PDF) in Friedländer Condensation of o-aminonitrile with Carbonyl Compounds

Abstract

Since the discovery of the new conversion, through intramolecular Pinner to Dimroth rearrangement to form a new skeleton product of dihydroquinazolinone in the normal reaction of Friendländer quinoline synthesis of o-aminonitriles and carbonyl compounds, systematic studies have shown that this conversion is a fast and efficient method for the synthesis of nitrogen-containing heterocyclic compounds, especially pyrimidinone derivatives. In 2008, we named this new transformation as a PDF conversion (a new conversion of dihydroquinolinone skeleton compounds formed from intramolecular Pinner to Dimroth rearrangement in the Friedländer quinoline synthesis). In this review, the research progress of PDF conversion is systematically summarized from the following aspects: the discovery of PDF conversion, the determination of the structure of new conversion products, the mechanism of PDF conversion, a new type of organic bifurcation reaction, controllable PDF conversion, the breakthrough of conventional PDF transformation forms, and the application of PDF conversion.