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

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

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2026, Volume: 193, Article number : 135153, Pages count : DOI: 10.1016/j.tet.2026.135153

Authors

Kolyadina Sofia ¹ , Kruchinin Andrey ¹ , Minyaev Mikhail ¹ , Bastrakov Maxim ¹ , Starosotnikov Alexey ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow, 119991, Russia

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.

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

Submitted:	Nov 28, 2025
Published online:	Jan 20, 2026

Web of science:	WOS:001674962300001
Scopus:	2-s2.0-105027561499
OpenAlex:	W7124581805

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