基于α-酮硫与硫酰胺的[2 + 3]环化诱捕的噻唑-5-硫酮的区域选择性合成

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2024-10-22 DOI:10.1002/ejoc.202401056

Xuehua Zhang, Yingxue Lin, Mingyang Guo, Kewen Xu, Jinhui Zhu, Jun Dong

{"title":"基于α-酮硫与硫酰胺的[2 + 3]环化诱捕的噻唑-5-硫酮的区域选择性合成","authors":"Xuehua Zhang, Yingxue Lin, Mingyang Guo, Kewen Xu, Jinhui Zhu, Jun Dong","doi":"10.1002/ejoc.202401056","DOIUrl":null,"url":null,"abstract":"Aiming to develop novel annulation reactions using sulfine intermediates, we have established a regioselective formal [2 + 3] cyclization reaction of α-keto sulfines generated from the elimination of arylacyl sulfoxides and thioamides. This new strategy allows for the synthesis of thiazole-5-thiones directly without catalysts or additives. The approach features a step-economic, one-pot characteristics via a tandem sequence of in situα-keto sulfines generation, regiospecifically nucleophilic attack or [3 + 2] cyclizatoin, dithioate (S=C−S−) skeletons formation, and subsequent intramolecular nucleophilic cyclization. This reaction also represents a novel method for constructing dithioate (S=C−S−) skeletons.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"24 1","pages":""},"PeriodicalIF":2.5000,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Regioselective Synthesis of Thiazole-5-thione Based on [2 + 3] Annulation Trapping of α-Keto Sulfine with Thioamide\",\"authors\":\"Xuehua Zhang, Yingxue Lin, Mingyang Guo, Kewen Xu, Jinhui Zhu, Jun Dong\",\"doi\":\"10.1002/ejoc.202401056\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Aiming to develop novel annulation reactions using sulfine intermediates, we have established a regioselective formal [2 + 3] cyclization reaction of α-keto sulfines generated from the elimination of arylacyl sulfoxides and thioamides. This new strategy allows for the synthesis of thiazole-5-thiones directly without catalysts or additives. The approach features a step-economic, one-pot characteristics via a tandem sequence of in situα-keto sulfines generation, regiospecifically nucleophilic attack or [3 + 2] cyclizatoin, dithioate (S=C−S−) skeletons formation, and subsequent intramolecular nucleophilic cyclization. This reaction also represents a novel method for constructing dithioate (S=C−S−) skeletons.\",\"PeriodicalId\":167,\"journal\":{\"name\":\"European Journal of Organic Chemistry\",\"volume\":\"24 1\",\"pages\":\"\"},\"PeriodicalIF\":2.5000,\"publicationDate\":\"2024-10-22\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"European Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1002/ejoc.202401056\",\"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":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/ejoc.202401056","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

为了利用硫中间体开发新的环化反应，我们建立了一种由芳基酰基硫醚和硫代酰胺消除产生的 α-酮基硫醚的区域选择性正规 [2 + 3] 环化反应。这种新策略无需催化剂或添加剂即可直接合成噻唑-5-硫酮。该方法的特点是通过原位生成α-酮基硫醚、特定区域亲核攻击或[3 + 2]环扎汀、形成二硫代酸酯（S=C-S-）骨架以及随后的分子内亲核环化等串联序列，实现一步经济、一锅式合成。该反应也是构建二硫酸盐（S=C-S-）骨架的一种新方法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Regioselective Synthesis of Thiazole-5-thione Based on [2 + 3] Annulation Trapping of α-Keto Sulfine with Thioamide

Aiming to develop novel annulation reactions using sulfine intermediates, we have established a regioselective formal [2 + 3] cyclization reaction of α-keto sulfines generated from the elimination of arylacyl sulfoxides and thioamides. This new strategy allows for the synthesis of thiazole-5-thiones directly without catalysts or additives. The approach features a step-economic, one-pot characteristics via a tandem sequence of in situα-keto sulfines generation, regiospecifically nucleophilic attack or [3 + 2] cyclizatoin, dithioate (S=C−S−) skeletons formation, and subsequent intramolecular nucleophilic cyclization. This reaction also represents a novel method for constructing dithioate (S=C−S−) skeletons.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.