New type of 4,5-annelated bicyclic sydnone imines. Assessment of sydnone imines effectiveness as plant stress protectants

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-08-27 DOI:10.1016/j.tet.2025.134904

Natalia V. Kalganova , Alena Soboleva , Ivan Godovikov , Tatiana Bilova , Andrej Frolov , Ludger Wessjohann , Il'ya A. Cherepanov

引用次数: 0

Abstract

We report the multistep synthesis of a new array of 4,5-annelated bicyclic sydnone imine – (6-cyano-1-substituted-[1,2,3]oxadiazolo[5,4-b]pyridin-1-ium-5-yl)amide hydrochlorides. These bicyclic compounds are featured with the mesomeric charge spread out over the two fused aromatic fragments. Thus, these molecules can be considered as a new type of sydnone imine. The molecular structures of the bicyclic compounds were investigated in detail by X-ray and ¹H, ¹³C, and ¹⁵N NMR studies. In addition, the characterization of these compounds and their synthetic intermediaries was undertaken to ascertain their effectiveness as potential plant stress protectants or herbicides.

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一类新的4,5-环合双环苯并亚胺。辛多酚亚胺作为植物逆境保护剂的有效性评价

我们报道了一组新的4,5-环合的双环辛酮亚胺-（6-氰基-1-取代-[1,2,3]恶二唑[5,4-b]吡啶-1-ium-5-基）酰胺氯化物的多步合成。这些双环化合物的特点是中聚体电荷分布在两个融合的芳香片段上。因此，这些分子可以被认为是一种新型的突触亚胺。通过x射线、1H、13C和15N核磁共振对双环化合物的分子结构进行了详细的研究。此外，还对这些化合物及其合成中间体进行了表征，以确定它们作为潜在植物胁迫保护剂或除草剂的有效性。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.