СИНТЕТИЧНІ ПІДХОДИ ДО ГІДРОВАНИХ ПІРИДО[b]АЗЕПІНІВ ТА ЇХНІХ БЕНЗАНЕЛЬОВАНИХ АНАЛОГІВ

СИНТЕТИЧНІ ПІДХОДИ ДО ГІДРОВАНИХ ПІРИДО[b]АЗЕПІНІВ ТА ЇХНІХ БЕНЗАНЕЛЬОВАНИХ АНАЛОГІВ

Pyrido[b]azepines are represented in the literature by four types of isomeric structures: pyrido[3,2-b] azepines, pyrido[2,3-b]azepines, pyrido[3,4-b] azepines and pyrido[4,3-b ]azepines. They belong to the structural analogues of 1-benzazepine - an attractive class of heterocycles with a strong pha...

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Date:2020
Main Authors: Danyliuk, Ivanna, Vovk, Mykhailo
Format: Article
Language:English
Published: V.I.Vernadsky Institute of General and Inorganic Chemistry 2020
Online Access:https://ucj.org.ua/index.php/journal/article/view/214
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spelling oai:ojs2.1444248.nisspano.web.hosting-test.net:article-2142020-09-28T12:34:36Z SYNTHETIC APPROACHES TO HYDROGENIZED PYRIDYL[b]AZEPINE AND THEIR BENZENELYLATED ANALOGUES СИНТЕТИЧЕСКИЕ ПОДХОДЫ К ГИДРИРОВАННЫМ ПИРИДО[b]АЗЕПИНАМ И ИХ БЕНЗАННЕЛИРОВАННЫМ АНАЛОГАМ СИНТЕТИЧНІ ПІДХОДИ ДО ГІДРОВАНИХ ПІРИДО[b]АЗЕПІНІВ ТА ЇХНІХ БЕНЗАНЕЛЬОВАНИХ АНАЛОГІВ Danyliuk, Ivanna Vovk, Mykhailo pyrido[b]azepines, catalytic cyclization, radical reactions, Beckmann rearrangement, cycloalkylations. Pyrido[b]azepines are represented in the literature by four types of isomeric structures: pyrido[3,2-b] azepines, pyrido[2,3-b]azepines, pyrido[3,4-b] azepines and pyrido[4,3-b ]azepines. They belong to the structural analogues of 1-benzazepine - an attractive class of heterocycles with a strong pharmacological profile. They are also used as important molecular platforms in the construction of bioactive compounds. Analysis of the literature has shown that compounds that contain the pyrido[b]azepine fragment demonstrate antiviral, antimicrobial, and antitumor activity. They are knownas effective inhibitors of R1P1 kinase, ubiquitin- specific proteases (USPS), cyclin-dependent kinase (CDKS), and glycogen synthase kinase 3 (GSK-3), TRPM8 protein, and angiotensin I type 2 (AT2) receptors. Over the last decade, promising pharmacological properties of pyrido[b]azepine derivatives stimulated the development of fundamentally new methods of their synthesis as well as the improvement of known synthetic approaches. In general, among the various methods for the synthesis of hydrogenated pyrido[b] azepines and their benzanelated analogues, priority is currently given to approaches that include the formation of an azepine cycle via the intermolecular formation of C-N and C-C bonds. These mainly include catalytic cyclizations using cobalt, palladium, and rhodium compounds. Reactions of intramolecular radical difluoromethylarylation and diauryl peroxide-initiated radical azepine analelenization of the pyridine fragment are also of great importance. An interesting method for the synthesis of pyrido [2,3-b] azepin-5-one derivatives was developed on the basis of the Friedel-Crafts intramolecular cycloalkylations reaction. V.I.Vernadsky Institute of General and Inorganic Chemistry 2020-09-15 Article Article Organic chemistry Органическая xимия Органічна xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/214 10.33609/2708-129X.86.8.2020.101-110 Ukrainian Chemistry Journal; Vol. 86 No. 8 (2020): Ukrainian Chemistry Journal; 101-110 Украинский химический журнал; Том 86 № 8 (2020): Украинский химический журнал; 101-110 Український хімічний журнал; Том 86 № 8 (2020): Український хімічний журнал; 101-110 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/214/120
institution Ukrainian Chemistry Journal
baseUrl_str
datestamp_date 2020-09-28T12:34:36Z
collection OJS
language English
topic_facet pyrido[b]azepines
catalytic cyclization
radical reactions
Beckmann rearrangement
cycloalkylations.
format Article
author Danyliuk, Ivanna
Vovk, Mykhailo
spellingShingle Danyliuk, Ivanna
Vovk, Mykhailo
СИНТЕТИЧНІ ПІДХОДИ ДО ГІДРОВАНИХ ПІРИДО[b]АЗЕПІНІВ ТА ЇХНІХ БЕНЗАНЕЛЬОВАНИХ АНАЛОГІВ
author_facet Danyliuk, Ivanna
Vovk, Mykhailo
author_sort Danyliuk, Ivanna
title СИНТЕТИЧНІ ПІДХОДИ ДО ГІДРОВАНИХ ПІРИДО[b]АЗЕПІНІВ ТА ЇХНІХ БЕНЗАНЕЛЬОВАНИХ АНАЛОГІВ
title_short СИНТЕТИЧНІ ПІДХОДИ ДО ГІДРОВАНИХ ПІРИДО[b]АЗЕПІНІВ ТА ЇХНІХ БЕНЗАНЕЛЬОВАНИХ АНАЛОГІВ
title_full СИНТЕТИЧНІ ПІДХОДИ ДО ГІДРОВАНИХ ПІРИДО[b]АЗЕПІНІВ ТА ЇХНІХ БЕНЗАНЕЛЬОВАНИХ АНАЛОГІВ
title_fullStr СИНТЕТИЧНІ ПІДХОДИ ДО ГІДРОВАНИХ ПІРИДО[b]АЗЕПІНІВ ТА ЇХНІХ БЕНЗАНЕЛЬОВАНИХ АНАЛОГІВ
title_full_unstemmed СИНТЕТИЧНІ ПІДХОДИ ДО ГІДРОВАНИХ ПІРИДО[b]АЗЕПІНІВ ТА ЇХНІХ БЕНЗАНЕЛЬОВАНИХ АНАЛОГІВ
title_sort синтетичні підходи до гідрованих піридо[b]азепінів та їхніх бензанельованих аналогів
title_alt SYNTHETIC APPROACHES TO HYDROGENIZED PYRIDYL[b]AZEPINE AND THEIR BENZENELYLATED ANALOGUES
СИНТЕТИЧЕСКИЕ ПОДХОДЫ К ГИДРИРОВАННЫМ ПИРИДО[b]АЗЕПИНАМ И ИХ БЕНЗАННЕЛИРОВАННЫМ АНАЛОГАМ
description Pyrido[b]azepines are represented in the literature by four types of isomeric structures: pyrido[3,2-b] azepines, pyrido[2,3-b]azepines, pyrido[3,4-b] azepines and pyrido[4,3-b ]azepines. They belong to the structural analogues of 1-benzazepine - an attractive class of heterocycles with a strong pharmacological profile. They are also used as important molecular platforms in the construction of bioactive compounds. Analysis of the literature has shown that compounds that contain the pyrido[b]azepine fragment demonstrate antiviral, antimicrobial, and antitumor activity. They are knownas effective inhibitors of R1P1 kinase, ubiquitin- specific proteases (USPS), cyclin-dependent kinase (CDKS), and glycogen synthase kinase 3 (GSK-3), TRPM8 protein, and angiotensin I type 2 (AT2) receptors. Over the last decade, promising pharmacological properties of pyrido[b]azepine derivatives stimulated the development of fundamentally new methods of their synthesis as well as the improvement of known synthetic approaches. In general, among the various methods for the synthesis of hydrogenated pyrido[b] azepines and their benzanelated analogues, priority is currently given to approaches that include the formation of an azepine cycle via the intermolecular formation of C-N and C-C bonds. These mainly include catalytic cyclizations using cobalt, palladium, and rhodium compounds. Reactions of intramolecular radical difluoromethylarylation and diauryl peroxide-initiated radical azepine analelenization of the pyridine fragment are also of great importance. An interesting method for the synthesis of pyrido [2,3-b] azepin-5-one derivatives was developed on the basis of the Friedel-Crafts intramolecular cycloalkylations reaction.
publisher V.I.Vernadsky Institute of General and Inorganic Chemistry
publishDate 2020
url https://ucj.org.ua/index.php/journal/article/view/214
work_keys_str_mv AT danyliukivanna syntheticapproachestohydrogenizedpyridylbazepineandtheirbenzenelylatedanalogues
AT vovkmykhailo syntheticapproachestohydrogenizedpyridylbazepineandtheirbenzenelylatedanalogues
AT danyliukivanna sintetičeskiepodhodykgidrirovannympiridobazepinamiihbenzannelirovannymanalogam
AT vovkmykhailo sintetičeskiepodhodykgidrirovannympiridobazepinamiihbenzannelirovannymanalogam
AT danyliukivanna sintetičnípídhodidogídrovanihpíridobazepínívtaíhníhbenzanelʹovanihanalogív
AT vovkmykhailo sintetičnípídhodidogídrovanihpíridobazepínívtaíhníhbenzanelʹovanihanalogív
first_indexed 2025-09-24T17:43:34Z
last_indexed 2025-09-24T17:43:34Z
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