A Ring Opening–Annulation Reaction of Anthra[1,2-<i>d</i>][1,2,3]triazine-4,7,12(3<i>H</i>)-trione in the Presence of Pyridines as an Efficient Approach to the Construction of Naphtho[2,3-<i>H</i>]pyrido(quinolino)[2,1-<i>b</i>]quinazoline System

Abstract

The [1,2,3]triazin-4(3H)-one ring is a synthetically important molecular platform for a variety of chemical transformations. Despite this, currently, there has been little research on the reaction of the thermal opening of the [1,2,3]triazin-4(3H)-one nucleus. In this work, we describe the synthetic potential of anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-trione in the reaction of the thermal opening of a cycle following the [4+2]-cycloaddition reaction with a number of pyridine derivatives and quinoline. It is shown that this method is effective for the synthesis of the 6H-naphtho[2,3-H]pyrido(quinolino)[2,1-b]quinazoline-6,9,14-trione system. We also investigate the influence of the position of substituents in the structure of pyridine on the formation characteristics of the target products.

Keywords

• anthra[1,2-<i>d</i>][1,2,3]triazine-4,7,12(3<i>H</i>)-trione
• thermolysis
• iminoketene
• pyridines
• quinoline
• [4+2]-cycloaddition