Natalia V. Kalganova , Alena Soboleva , Ivan Godovikov , Tatiana Bilova , Andrej Frolov , Ludger Wessjohann , Il'ya A. Cherepanov
{"title":"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","authors":"Natalia V. Kalganova , Alena Soboleva , Ivan Godovikov , Tatiana Bilova , Andrej Frolov , Ludger Wessjohann , Il'ya A. Cherepanov","doi":"10.1016/j.tet.2025.134904","DOIUrl":null,"url":null,"abstract":"<div><div>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-<em>b</em>]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 <sup>1</sup>H, <sup>13</sup>C, and <sup>15</sup>N 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.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"187 ","pages":"Article 134904"},"PeriodicalIF":2.2000,"publicationDate":"2025-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"New type of 4,5-annelated bicyclic sydnone imines. Assessment of sydnone imines effectiveness as plant stress protectants\",\"authors\":\"Natalia V. Kalganova , Alena Soboleva , Ivan Godovikov , Tatiana Bilova , Andrej Frolov , Ludger Wessjohann , Il'ya A. Cherepanov\",\"doi\":\"10.1016/j.tet.2025.134904\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>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-<em>b</em>]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 <sup>1</sup>H, <sup>13</sup>C, and <sup>15</sup>N 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.</div></div>\",\"PeriodicalId\":437,\"journal\":{\"name\":\"Tetrahedron\",\"volume\":\"187 \",\"pages\":\"Article 134904\"},\"PeriodicalIF\":2.2000,\"publicationDate\":\"2025-08-27\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040402025004600\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402025004600","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
New type of 4,5-annelated bicyclic sydnone imines. Assessment of sydnone imines effectiveness as plant stress protectants
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.
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.