Синтетичні підходи до гідрованих піридо[b]азепінів та їхніх бензанельованих аналогів
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Date
2020
Authors
Данилюк, Іванна
Вовк, Михайло
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Abstract
У мікроогляді узагальнено літературні джерела за методами синтезу функціональних і бензанельованих похідних гідрованих піридо[b]азепінів за останні 10 років, які класифіковано на
4 основні групи: процеси каталітичного циклоутворення, радикальні реакції, перегрупування
Бекмана та циклоацилювання за Фріделем – Крафтсом.
В микрообзоре обобщены литературные источники по методам синтеза функциональных и бензаннелированных производных гидрированных пиридо[b]азепинов за последние 10 лет, которые классифицированы на 4 основные группы: процессы каталитического циклообразования, радикальные реакции, перегруппировка Бекмана и циклоацилирование по Фриделю – Крафтсу.
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 molecu- lar 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 known as effective inhibitors of R1P1 kinase, ubiquitin-specific proteases (USPS), cyclin-dependent kinase (CDKS), and glycogen synthase kinase 3 (GSK-3), TRPM8 protein, and angiotensin II type 2 (AT2) receptors. Over the last decade, promising pharmacological properties of pyrido[b]azepine derivatives stimulated the development of fun- damentally 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.
В микрообзоре обобщены литературные источники по методам синтеза функциональных и бензаннелированных производных гидрированных пиридо[b]азепинов за последние 10 лет, которые классифицированы на 4 основные группы: процессы каталитического циклообразования, радикальные реакции, перегруппировка Бекмана и циклоацилирование по Фриделю – Крафтсу.
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 molecu- lar 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 known as effective inhibitors of R1P1 kinase, ubiquitin-specific proteases (USPS), cyclin-dependent kinase (CDKS), and glycogen synthase kinase 3 (GSK-3), TRPM8 protein, and angiotensin II type 2 (AT2) receptors. Over the last decade, promising pharmacological properties of pyrido[b]azepine derivatives stimulated the development of fun- damentally 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.
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Keywords
піридо[b]азепіни, каталітичне циклоутворення, радикальні реакції, перегрупування Бекмана, циклоацилювання, стаття, pyrido[b]azepines, catalytic cyclization, radical reactions, Beckmann rearrangement, cycloalkylations, пиридо[b]азепины, каталитическое циклообразование, радикальне реакции, перегруппировка Бекмана, циклоацилирование
Citation
Данилюк І. Ю. Синтетичні підходи до гідрованих піридо[b]азепінів та їхніх бензанельованих аналогів / І. Ю. Данилюк, М. В. Вовк // Український хімічний журнал. - 2020. - Т. 86, № 8. - С. 101-110.