Oxidative Cyclization of 5<i>H</i>-Chromeno[2,3-<i>b</i>]pyridines to Benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED

Abstract

Oxidative cyclization is one of the most significant reactions in organic synthesis. Naphthyridine derivatives are often used as luminescence materials in molecular recognition because of their rigid planar structure and as new drugs. Organic light-emitting diodes (OLEDs) have rapidly grown as one of the leading technologies for full-color display panels and eco-friendly lighting sources. In this work, we propose the synthesis of previously unknown benzo[b]chromeno[4,3,2-de][1,6]naphthyridines via intermolecular oxidative cyclization of 5-(2-hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridines in formic acid. The investigation of the reaction mechanism using 1H-NMR monitoring made it possible to confirm the proposed mechanism of the transformation. The structure of synthesized benzo[b]chromeno[4,3,2-de][1,6]naphthyridines was confirmed by 2D-NMR spectroscopy. Such a rigid geometry of synthesized compounds is desired to minimize non-radiative energy losses in OLEDs. The quantum chemical calculations are also presented in the study.

Keywords

• benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridine
• chromeno[2,3-<i>b</i>]pyridine
• computer evaluation
• formic acid
• NMR study
• oxidative cyclization