Dmitriy Mertsalov, Dmitriy Shchevnikov, Lala Lovtsevich, Roman A Novikov, Victor N Khrustalev, Mikhail S. Grigoriev, Anna Romanycheva, Anton Shetnev, Olga Bychkova, Alexey Trenin, Vladimir P. Zaytsev
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引用次数: 0
摘要
N-糠基烯丙基胺与多种异氰酸酯、异硫氰酸酯和异硒氰酸酯发生反应,在一个合成阶段形成 3a,6-环氧异吲哚核。相互作用顺序包括两个连续步骤:亲核加成反应和分子内 Dielse-Alder 呋喃е(IMDAF)反应。研究人员对所提出方法的范围和局限性进行了深入研究,发现关键的[4 + 2]环加成步骤是通过外蜕变状态进行的,只形成目标杂环的单一非对映异构体。通过动态温度核磁共振分析,可以全面研究核磁共振信号凝聚的情况,并确定 O → Se 转变过程中的凝聚温度。确定了所获化合物对敏感酵母菌白色念珠菌、真菌黑曲霉和细菌(包括金黄色葡萄球菌、黄绿微球菌和荧光假单胞菌)的抗菌特性。
The Short Route to Chalcogenurea-substituted 3а,6-Epoxyisoindoles via an Intramolecular Diels–Alder Furan (IMDAF) Reaction. Antibacterial and Antifungal activity
N-Furfuryl allylamines react with a broad range of isocyanates, isothiocyanates, isoselenocyanates with the formation of a 3a,6-epoxyisoindole core in one synthetic stage. The interaction sequence involves two consecutive steps: the nucleophilic addition reaction and the intramolecular Dielse-Alder furanе (IMDAF) reaction. The scope and limitations of the proposed method were thoroughly investigated, and it was revealed that the key [4 + 2] cycloaddition step proceeds through an exo-transition state, giving rise to the exclusive formation of a single diastereomer of the target heterocycle. Dynamic temperature NMR analysis allowed to fully investigating a case of coalescence of NMR signals and determined the coalescence temperature during the transition O → Se. The antimicrobial properties of the obtained compounds against sensitive strains of yeast Candida albicans, fungus Aspergillus niger and bacteria including Staphylococcus aureus, Micrococcus luteus, Pseudomonas fluorescens were identified.