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A Ring Opening–Annulation Reaction of Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-trione in the Presence of Pyridines as an Efficient Approach to the Construction of Naphtho[2,3-H]pyrido(quinolino)[2,1-b]quinazoline System
Authors:Viktor Zvarych  Maryna Stasevych  Eduard Rusanov  Mykhailo Vovk
Affiliation:1.Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, 79013 Lviv, Ukraine;2.Department of Chemistry of Functional Heterocyclic Systems, Institute of Organic Chemistry of National Academy of Sciences of Ukraine, 02660 Kyiv, Ukraine
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-d][1,2,3]triazine-4,7,12(3H)-trione   thermolysis   iminoketene   pyridines   quinoline   [4+2]-cycloaddition
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