A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.
Molecules. 2021 Sep 14;26(18):5579. doi: 10.3390/molecules26185579.
A novel family of [1,4]thiazino[2,3,4-]quinolin-4-ium derivatives was synthesized by annulation reactions of 8-quinolinesulfenyl chloride with unsaturated heteroatom and heterocyclic compounds. It was found that the reactions with 4-pentenoic and 5-hexenoic acids, allyl chloride and bromide, allyl cyanate and vinyl heterocyclic compounds (-vinyl pyrrolidin-2-one and 1-vinylimidazole) proceeded in a regioselective mode but with the opposite regiochemistry. The reactions with vinyl heterocyclic compounds included electrophilic addition of the sulfur atom of 8-quinolinesulfenyl chloride to the β-carbon atom of the vinyl group. In the case of other substrates, the annulation proceeded with the attachment of the sulfur atom to the α-carbon atom of the vinyl group. The antibacterial activity of novel water-soluble compounds against , and was evaluated. Compounds with high antibacterial activity were found.
通过 8-喹啉亚磺酰氯与不饱和杂原子和杂环化合物的环化反应，合成了一类新型的[1,4]噻嗪并[2,3,4-]喹啉-4-鎓衍生物。研究发现，与 4-戊烯酸和 5-己烯酸、烯丙基氯和溴、烯丙基氰酸盐和乙烯基杂环化合物（-乙烯基吡咯烷-2-酮和 1-乙烯基咪唑）的反应具有区域选择性，但反应的区域化学性质相反。与乙烯基杂环化合物的反应包括 8-喹啉亚磺酰氯的硫原子对乙烯基的β-碳原子的亲电加成。在其他底物的情况下，环化反应是通过硫原子与乙烯基的α-碳原子连接进行的。评估了新型水溶性化合物对 、 和 的抗菌活性。发现了具有高抗菌活性的化合物。
