Cargando…

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

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Zvarych, Viktor, Stasevych, Maryna, Rusanov, Eduard, Vovk, Mykhailo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9505032/
https://www.ncbi.nlm.nih.gov/pubmed/36144663
http://dx.doi.org/10.3390/molecules27185927
_version_ 1784796371215187968
author Zvarych, Viktor
Stasevych, Maryna
Rusanov, Eduard
Vovk, Mykhailo
author_facet Zvarych, Viktor
Stasevych, Maryna
Rusanov, Eduard
Vovk, Mykhailo
author_sort Zvarych, Viktor
collection PubMed
description 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.
format Online
Article
Text
id pubmed-9505032
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-95050322022-09-24 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 Zvarych, Viktor Stasevych, Maryna Rusanov, Eduard Vovk, Mykhailo Molecules Article 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. MDPI 2022-09-12 /pmc/articles/PMC9505032/ /pubmed/36144663 http://dx.doi.org/10.3390/molecules27185927 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zvarych, Viktor
Stasevych, Maryna
Rusanov, Eduard
Vovk, Mykhailo
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9505032/
https://www.ncbi.nlm.nih.gov/pubmed/36144663
http://dx.doi.org/10.3390/molecules27185927
work_keys_str_mv AT zvarychviktor aringopeningannulationreactionofanthra12d123triazine47123htrioneinthepresenceofpyridinesasanefficientapproachtotheconstructionofnaphtho23hpyridoquinolino21bquinazolinesystem
AT stasevychmaryna aringopeningannulationreactionofanthra12d123triazine47123htrioneinthepresenceofpyridinesasanefficientapproachtotheconstructionofnaphtho23hpyridoquinolino21bquinazolinesystem
AT rusanoveduard aringopeningannulationreactionofanthra12d123triazine47123htrioneinthepresenceofpyridinesasanefficientapproachtotheconstructionofnaphtho23hpyridoquinolino21bquinazolinesystem
AT vovkmykhailo aringopeningannulationreactionofanthra12d123triazine47123htrioneinthepresenceofpyridinesasanefficientapproachtotheconstructionofnaphtho23hpyridoquinolino21bquinazolinesystem
AT zvarychviktor ringopeningannulationreactionofanthra12d123triazine47123htrioneinthepresenceofpyridinesasanefficientapproachtotheconstructionofnaphtho23hpyridoquinolino21bquinazolinesystem
AT stasevychmaryna ringopeningannulationreactionofanthra12d123triazine47123htrioneinthepresenceofpyridinesasanefficientapproachtotheconstructionofnaphtho23hpyridoquinolino21bquinazolinesystem
AT rusanoveduard ringopeningannulationreactionofanthra12d123triazine47123htrioneinthepresenceofpyridinesasanefficientapproachtotheconstructionofnaphtho23hpyridoquinolino21bquinazolinesystem
AT vovkmykhailo ringopeningannulationreactionofanthra12d123triazine47123htrioneinthepresenceofpyridinesasanefficientapproachtotheconstructionofnaphtho23hpyridoquinolino21bquinazolinesystem