{"title":"在不同亲核条件下合成 BIM 及其类似物的级联方法","authors":"","doi":"10.1016/j.tetlet.2024.155248","DOIUrl":null,"url":null,"abstract":"<div><p>We report here a cascade synthetic approach to prepare 3,3′-bis(indolyl)methanes (BIMs) and analogues from single reactant 1<em>H</em>-indole-3-carbaldehydes under the reductive condition using NaBH<sub>4</sub>. Uniformly, in another strategy, 1<em>H</em>-indole-3-carbaldehydes produced BIMs as a cascade product under Grignard reaction conditions. This is the first application of organometallic and reductive nucleophilic condition, where indole-3-carbaldehydes underwent NaBH<sub>4</sub> reduction/ methyl Grignard addition to form 1°/2° alcohol followed by elimination and subsequent addition of another molecule of indole aldehyde provided symmetric BIMs as unambiguous cascade products (22 analogues) in good to excellent yields.</p></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-08-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Cascade approach to synthesize BIMs and analogues in different nucleophilic conditions\",\"authors\":\"\",\"doi\":\"10.1016/j.tetlet.2024.155248\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>We report here a cascade synthetic approach to prepare 3,3′-bis(indolyl)methanes (BIMs) and analogues from single reactant 1<em>H</em>-indole-3-carbaldehydes under the reductive condition using NaBH<sub>4</sub>. Uniformly, in another strategy, 1<em>H</em>-indole-3-carbaldehydes produced BIMs as a cascade product under Grignard reaction conditions. This is the first application of organometallic and reductive nucleophilic condition, where indole-3-carbaldehydes underwent NaBH<sub>4</sub> reduction/ methyl Grignard addition to form 1°/2° alcohol followed by elimination and subsequent addition of another molecule of indole aldehyde provided symmetric BIMs as unambiguous cascade products (22 analogues) in good to excellent yields.</p></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-08-11\",\"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/S0040403924003435\",\"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/S0040403924003435","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Cascade approach to synthesize BIMs and analogues in different nucleophilic conditions
We report here a cascade synthetic approach to prepare 3,3′-bis(indolyl)methanes (BIMs) and analogues from single reactant 1H-indole-3-carbaldehydes under the reductive condition using NaBH4. Uniformly, in another strategy, 1H-indole-3-carbaldehydes produced BIMs as a cascade product under Grignard reaction conditions. This is the first application of organometallic and reductive nucleophilic condition, where indole-3-carbaldehydes underwent NaBH4 reduction/ methyl Grignard addition to form 1°/2° alcohol followed by elimination and subsequent addition of another molecule of indole aldehyde provided symmetric BIMs as unambiguous cascade products (22 analogues) in good to excellent yields.
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.