{"title":"阴离子驱动三氟甲基 N-芳基肼的 CF 键裂解以组装 N-杂环","authors":"","doi":"10.1016/j.tetlet.2024.155328","DOIUrl":null,"url":null,"abstract":"<div><div>Herein we report an efficient and convenient method for synthesizing 1<em>H</em>-benzo[<em>d</em>]imidazoles via a base-promoted reaction of readily available α-CF<sub>3</sub> ketone-derived hydrazones with <em>o</em>-phenylenediamines. The key innovation is the anion-driven triple-cleavage of the C<img>F bond in the CF<sub>3</sub> group, which acts as a C1 synthon at the 2-position of the 1<em>H</em>-benzo[<em>d</em>]imidazole. This novel approach simplifies the synthesis and can be extended to the preparation of benzo[<em>d</em>]oxazoles and benzo[<em>d</em>]thiazoles. Our method offers a versatile and robust platform for the synthesis of important heterocyclic compounds, with potential applications in medicinal chemistry and drug discovery.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Anion-driven CF bond cleavage of trifluoromethyl N-aryl hydrazones toward the assembly of N-heterocycles\",\"authors\":\"\",\"doi\":\"10.1016/j.tetlet.2024.155328\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Herein we report an efficient and convenient method for synthesizing 1<em>H</em>-benzo[<em>d</em>]imidazoles via a base-promoted reaction of readily available α-CF<sub>3</sub> ketone-derived hydrazones with <em>o</em>-phenylenediamines. The key innovation is the anion-driven triple-cleavage of the C<img>F bond in the CF<sub>3</sub> group, which acts as a C1 synthon at the 2-position of the 1<em>H</em>-benzo[<em>d</em>]imidazole. This novel approach simplifies the synthesis and can be extended to the preparation of benzo[<em>d</em>]oxazoles and benzo[<em>d</em>]thiazoles. Our method offers a versatile and robust platform for the synthesis of important heterocyclic compounds, with potential applications in medicinal chemistry and drug discovery.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-10-11\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403924004234\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924004234","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Anion-driven CF bond cleavage of trifluoromethyl N-aryl hydrazones toward the assembly of N-heterocycles
Herein we report an efficient and convenient method for synthesizing 1H-benzo[d]imidazoles via a base-promoted reaction of readily available α-CF3 ketone-derived hydrazones with o-phenylenediamines. The key innovation is the anion-driven triple-cleavage of the CF bond in the CF3 group, which acts as a C1 synthon at the 2-position of the 1H-benzo[d]imidazole. This novel approach simplifies the synthesis and can be extended to the preparation of benzo[d]oxazoles and benzo[d]thiazoles. Our method offers a versatile and robust platform for the synthesis of important heterocyclic compounds, with potential applications in medicinal chemistry and drug discovery.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.