{"title":"2-碘苯并胺与氰酸钾催化偶联合成n3取代-喹唑啉-2,4(1H,3H)-二酮","authors":"Ali Nasirpour , Zarrin Ghasemi , Seyed Abolfazl Hosseini-Yazdi , Morgane Poupon , Cinthia Antunes Correa","doi":"10.1016/j.rechem.2025.102204","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, we disclosed the synthesis of <em>N</em>3-substituted-quinazoline-2,4(1<em>H</em>,3<em>H</em>)-diones via the consecutive copper-catalyzed coupling/annulation of 2-iodobenzamides and KOCN. This transformation is characterized by the in situ-generation of arylisocyante through C(<em>sp</em><sup><em>2</em></sup>)-N(<em>sp</em><sup><em>2</em></sup>) bond formation, which enriches the library of preparation quinazolindiones. Moreover, it is worth noting that replacing the iodo group with bromo also produced a comparable yield of the corresponding quinazolinedione derived under the present conditions.</div></div>","PeriodicalId":420,"journal":{"name":"Results in Chemistry","volume":"15 ","pages":"Article 102204"},"PeriodicalIF":4.2000,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of N3-substituted-quinazoline-2,4(1H,3H)-diones via CuI-catalyzed coupling of 2-iodobenzamides with potassium cyanate\",\"authors\":\"Ali Nasirpour , Zarrin Ghasemi , Seyed Abolfazl Hosseini-Yazdi , Morgane Poupon , Cinthia Antunes Correa\",\"doi\":\"10.1016/j.rechem.2025.102204\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Herein, we disclosed the synthesis of <em>N</em>3-substituted-quinazoline-2,4(1<em>H</em>,3<em>H</em>)-diones via the consecutive copper-catalyzed coupling/annulation of 2-iodobenzamides and KOCN. This transformation is characterized by the in situ-generation of arylisocyante through C(<em>sp</em><sup><em>2</em></sup>)-N(<em>sp</em><sup><em>2</em></sup>) bond formation, which enriches the library of preparation quinazolindiones. Moreover, it is worth noting that replacing the iodo group with bromo also produced a comparable yield of the corresponding quinazolinedione derived under the present conditions.</div></div>\",\"PeriodicalId\":420,\"journal\":{\"name\":\"Results in Chemistry\",\"volume\":\"15 \",\"pages\":\"Article 102204\"},\"PeriodicalIF\":4.2000,\"publicationDate\":\"2025-05-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Results in Chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S2211715625001870\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/3/19 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Results in Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2211715625001870","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/3/19 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Synthesis of N3-substituted-quinazoline-2,4(1H,3H)-diones via CuI-catalyzed coupling of 2-iodobenzamides with potassium cyanate
Herein, we disclosed the synthesis of N3-substituted-quinazoline-2,4(1H,3H)-diones via the consecutive copper-catalyzed coupling/annulation of 2-iodobenzamides and KOCN. This transformation is characterized by the in situ-generation of arylisocyante through C(sp2)-N(sp2) bond formation, which enriches the library of preparation quinazolindiones. Moreover, it is worth noting that replacing the iodo group with bromo also produced a comparable yield of the corresponding quinazolinedione derived under the present conditions.
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