Viacheslav Lysenko , Anton Portiankin , Tetiana Shvydenko , Kostiantyn Shvydenko , Svitlana Shishkina , Aleksandr Kostyuk
{"title":"Synthesis and functionalization of 6,7-dihydro-5H-pyrrolo[1,2-c]imidazole","authors":"Viacheslav Lysenko , Anton Portiankin , Tetiana Shvydenko , Kostiantyn Shvydenko , Svitlana Shishkina , Aleksandr Kostyuk","doi":"10.1080/00397911.2023.2188221","DOIUrl":null,"url":null,"abstract":"<div><p>Starting from readily available aminocarbonyl compounds Marckwald reaction was used for the preparation of 6,7-dihydro-5H-pyrrolo[1,2-c]imidazoles. The two-step procedure afforded the product in high yield and can be used for preparation of bulk quantities. Their further reactions with various electrophiles were studied giving previously unknown functionalized derivatives. The reaction with silylformamidine that exists in an equilibrium with its carbenic form afforded C-silyl derivative. Various halogen derivatives were prepared and used as starting materials. • Commercially available starting materials</p><p>• High yield methods</p><p>• Can be used for bulk synthesis of unsubstituted imidazoles</p><p>• Polyfunctional core</p><p>• 22 examples</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"53 9","pages":"Pages 615-624"},"PeriodicalIF":1.8000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S003979112300245X","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Starting from readily available aminocarbonyl compounds Marckwald reaction was used for the preparation of 6,7-dihydro-5H-pyrrolo[1,2-c]imidazoles. The two-step procedure afforded the product in high yield and can be used for preparation of bulk quantities. Their further reactions with various electrophiles were studied giving previously unknown functionalized derivatives. The reaction with silylformamidine that exists in an equilibrium with its carbenic form afforded C-silyl derivative. Various halogen derivatives were prepared and used as starting materials. • Commercially available starting materials
• High yield methods
• Can be used for bulk synthesis of unsubstituted imidazoles
期刊介绍：
Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.
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