A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., 664033 Irkutsk, Russia.
Chemistry Department, Irkutsk State University, Karl Marx Str., 1, 664003 Irkutsk, Russia.
Molecules. 2022 Oct 11;27(20):6785. doi: 10.3390/molecules27206785.
The article is devoted to heterocyclization of bis(2-chloroprop-2-en-1-yl)sulfide which proceeds in hydrazine hydrate-alkali medium and leads to formation of thiophene and pyrrole derivatives: previously described 4,5,9,10-tetrahydrocycloocta[1,2-c;5,8-c']dithiophene, as well as unknown hydrazone of 5-methylidene-3-methyldihydrothiophen-2-one and 1-amino-2-(propynylsulfanylpropenylsulfanyl)-3,5-dimethylpyrrole. Tentative mechanisms for the formation of the heterocyclic products are discussed. Obtained hydrazone of 5-methylidene-3-methyldihydrothiophen-2-one was used for the synthesis of a range of azine derivatives and in oxidation process with SeO. The found reactions open up expedient approaches to the formation of various hardly accessible thiophene and pyrrole compounds from 2,3-dichloropropene and elemental sulfur as starting reagents.
本文致力于研究双（2-氯-2-丙烯基）二硫醚的杂环化反应，该反应在水合肼-碱介质中进行，生成噻吩和吡咯衍生物：以前描述的 4,5,9,10-四氢环辛[1,2-c;5,8-c']二噻吩，以及 5-亚甲基-3-亚甲基二氢噻吩-2-酮和 1-氨基-2-（丙炔基硫基）丙烯基硫基）-3,5-二甲基吡咯的未知腙。讨论了形成杂环产物的可能机制。所得到的 5-亚甲基-3-亚甲基二氢噻吩-2-酮腙用于一系列嗪衍生物的合成，并在 SeO 的氧化过程中使用。发现的反应为从 2,3-二氯丙烯和元素硫作为起始试剂形成各种难以获得的噻吩和吡咯化合物提供了便利的方法。
