Dearomative (3 + 2) and (4 + 2) Cycloadditions of [1,2,4]Triazolo[1,5- a ]pyridines: Rapid Access to Polycyclic Triazole-Fused Skeletons

Dearomative (3 + 2) and (4 + 2) Cycloadditions of [1,2,4]Triazolo[1,5- a ]pyridines: Rapid Access to Polycyclic Triazole-Fused Skeletons Научная публикация

Журнал

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Вых. Данные

Год: 2025, Том: 90, Номер: 46, Страницы: 16546-16554 Страниц : 9 DOI: 10.1021/acs.joc.5c02157

Авторы

Kruchinin Andrey ¹ , Bastrakov Maxim ¹ , Minyaev Mikhail ¹ , Antropova Olga ¹ , Chaliy Vasiliy ¹ , Medvedev Michael ¹ , Starosotnikov Alexey ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect, 47, 119991 Moscow, Russian Federation

1,3-Dipolar cycloaddition of nonstabilized N-methyl azomethine ylide with electron-poor [1,2,4]triazolo[1,5-a]pyridines was studied. 6,8-Dinitro derivatives afforded bis-adducts of 2 equiv of 1,3-dipole, while mononitro [1,2,4]triazolo[1,5-a]pyridines gave various adducts depending on the nature of substituents in the pyridine cycle. Isoelectronic (4 + 2) cycloaddition of electron-rich 1,3-dienes proceeds only with the most electrophilic 6,8-dinitro[1,2,4]triazolo[1,5-a]pyridines to give three- and four-nuclear polycyclic systems. Both reactions were found to be diastereoselective, generally leading to trans-(bis)adducts.

Kruchinin A. , Bastrakov M. , Minyaev M. , Antropova O. , Chaliy V. , Medvedev M. , Starosotnikov A.
Dearomative (3 + 2) and (4 + 2) Cycloadditions of [1,2,4]Triazolo[1,5- a ]pyridines: Rapid Access to Polycyclic Triazole-Fused Skeletons
Journal of Organic Chemistry. 2025. V.90. N46. P.16546-16554. DOI: 10.1021/acs.joc.5c02157 WOS Scopus OpenAlex

Web of science:	WOS:001611280000001
Scopus:	2-s2.0-105023318567
OpenAlex:	W4416068544

БД	Цитирований
OpenAlex	Нет цитирований
Scopus	Нет цитирований