{"title":"Solvent effects in copper(I)-mediated 5-endo cyclisation of secondary bromo-enamides","authors":"Andrew J Clark , Colin P Dell , John P McDonagh","doi":"10.1016/S1387-1609(01)01275-0","DOIUrl":null,"url":null,"abstract":"<div><p>Secondary bromoenamides <strong>5</strong>, <strong>14-18</strong>, <strong>32</strong> and <strong>33</strong> undergo efficient 5-<em>endo</em> cyclisation reactions to give α,β-unsaturated monoene lactams <strong>9</strong>, <strong>19–23</strong>, <strong>34</strong> and <strong>35</strong> under atom transfer conditions mediated by CuBr and the tripyridylamine <strong>6</strong> in refluxing toluene (59–87%). Changing the solvent to refluxing 1,2-dichloroethane furnishes α,β-unsaturated diene lactams <strong>26-31</strong>, <strong>36</strong>, and <strong>37</strong> instead (42–86%).</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 575-579"},"PeriodicalIF":0.0000,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01275-0","citationCount":"2","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1387160901012750","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 2
Abstract
Secondary bromoenamides 5, 14-18, 32 and 33 undergo efficient 5-endo cyclisation reactions to give α,β-unsaturated monoene lactams 9, 19–23, 34 and 35 under atom transfer conditions mediated by CuBr and the tripyridylamine 6 in refluxing toluene (59–87%). Changing the solvent to refluxing 1,2-dichloroethane furnishes α,β-unsaturated diene lactams 26-31, 36, and 37 instead (42–86%).
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