{"title":"Synthesis of cyclopentane annulated δ-lactams via diazomethane-mediated CC bond cleavage of α-keto N,O-hemiaminals","authors":"Hari Mangeswara Rao Gorle, Satwinder Singh Marok","doi":"10.1002/jhet.4829","DOIUrl":null,"url":null,"abstract":"<p>Diazomethane-mediated C-C bond cleavage of α-keto <i>N,O</i>-hemiaminals was investigated for the first time. Diazomethane as a reagent result C-C bond cleavage of norbornyl α-keto <i>N,O</i>-hemiaminals, Grob-like fragmentation, lead to the formation of cyclopentane annulated δ-lactams in excellent yields. We have synthesized the precursor norbornyl α-keto <i>N,O</i>-hemiaminal by the nucleophilic displacement of halogen of norbornyl α-diketone with the various amines.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1070-1074"},"PeriodicalIF":2.0000,"publicationDate":"2024-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Heterocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/jhet.4829","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
Abstract
Diazomethane-mediated C-C bond cleavage of α-keto N,O-hemiaminals was investigated for the first time. Diazomethane as a reagent result C-C bond cleavage of norbornyl α-keto N,O-hemiaminals, Grob-like fragmentation, lead to the formation of cyclopentane annulated δ-lactams in excellent yields. We have synthesized the precursor norbornyl α-keto N,O-hemiaminal by the nucleophilic displacement of halogen of norbornyl α-diketone with the various amines.
期刊介绍：
The Journal of Heterocyclic Chemistry is interested in publishing research on all aspects of heterocyclic chemistry, especially development and application of efficient synthetic methodologies and strategies for the synthesis of various heterocyclic compounds. In addition, Journal of Heterocyclic Chemistry promotes research in other areas that contribute to heterocyclic synthesis/application, such as synthesis design, reaction techniques, flow chemistry and continuous processing, multiphase catalysis, green chemistry, catalyst immobilization and recycling.
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