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Synthesis and nucleophilic dearomatization of novel [1,2,4]triazolo[1,5-a]pyrimidines Научная публикация

Журнал Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416
Вых. Данные Год: 2026, Том: 193, Номер статьи : 135153, Страниц : DOI: 10.1016/j.tet.2026.135153
Авторы Kolyadina Sofia 1 , Kruchinin Andrey 1 , Minyaev Mikhail 1 , Bastrakov Maxim 1 , Starosotnikov Alexey 1
Организации
1 N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow, 119991, Russia

Реферат: A number of novel 2-R-6-nitro[1,2,4]triazolo[1,5-a]pyrimidines were synthesized. Their reactions with neutral C-nucleophiles (1,3-dicarbonyl compounds, indoles, polyphenols) proceeded under mild conditions (room temperature, no base or catalyst) giving rise to stable 1,4-adducts to pyrimidine ring. On the basis of 7-amino-6-nitro[1,2,4]triazolo[1,5-a]pyrimidines, a method was developed for the preparation of the previously unknown heterocyclic systems, namely [1,2,4]triazolo[1,5-a]pyrimidines fused with 1,2,5-oxa-, thia- and selenadiazole rings. These new heterocycles were found to undergo facile dearomatization under the action of 1,3-dicarbonyl compounds and π-excessive (het)arenes to give 1,2-adducts to pyrimidine ring. The possibility of oxidative rearomatization of the obtained adducts under the action of DDQ was demonstrated.
Библиографическая ссылка: Kolyadina S. , Kruchinin A. , Minyaev M. , Bastrakov M. , Starosotnikov A.
Synthesis and nucleophilic dearomatization of novel [1,2,4]triazolo[1,5-a]pyrimidines
Tetrahedron. 2026. V.193. 135153 . DOI: 10.1016/j.tet.2026.135153 WOS Scopus OpenAlex
Даты:
Поступила в редакцию: 28 нояб. 2025 г.
Опубликована online: 20 янв. 2026 г.
Идентификаторы БД:
Web of science: WOS:001674962300001
Scopus: 2-s2.0-105027561499
OpenAlex: W7124581805
Цитирование в БД:
БД Цитирований
OpenAlex Нет цитирований
Scopus Нет цитирований
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