Km Roshani, Mohammad Saim Raza, Rama Krishna Peddinti
{"title":"由对位醌甲酰胺和α-亚烷基琥珀酰亚胺在碱促进下构建 2H-色烯-2-酮和色烯并[2,3-c]吡咯支架的化学发散作用。","authors":"Km Roshani, Mohammad Saim Raza, Rama Krishna Peddinti","doi":"10.1021/acs.orglett.4c03436","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, we evolve a base-promoted synthesis of 2<i>H</i>-chromen-2-one and chromeno[2,3-<i>c</i>]pyrrole scaffolds via (4 + 2) annulation of α-alkylidene succinimides with 2-hydroxyphenyl-substituted <i>para</i>-quinone methides (<i>p</i>-QMs). Extremely selective and switchable cyclizations were obtained by modifying the base. This metal-free protocol is highlighted by its mild reaction conditions and broad substrate scope, and the viability of the existing protocol was additionally illustrated by gram-scale synthesis and further modification. Several control experiments were performed to understand the reaction mechanism.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Base-Promoted Chemodivergent Construction of 2<i>H</i>-Chromen-2-one and Chromeno[2,3-<i>c</i>]pyrrole Scaffolds from <i>para</i>-Quinone Methides and α-Alkylidene Succinimides.\",\"authors\":\"Km Roshani, Mohammad Saim Raza, Rama Krishna Peddinti\",\"doi\":\"10.1021/acs.orglett.4c03436\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Herein, we evolve a base-promoted synthesis of 2<i>H</i>-chromen-2-one and chromeno[2,3-<i>c</i>]pyrrole scaffolds via (4 + 2) annulation of α-alkylidene succinimides with 2-hydroxyphenyl-substituted <i>para</i>-quinone methides (<i>p</i>-QMs). Extremely selective and switchable cyclizations were obtained by modifying the base. This metal-free protocol is highlighted by its mild reaction conditions and broad substrate scope, and the viability of the existing protocol was additionally illustrated by gram-scale synthesis and further modification. Several control experiments were performed to understand the reaction mechanism.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2024-10-11\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.4c03436\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c03436","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Base-Promoted Chemodivergent Construction of 2H-Chromen-2-one and Chromeno[2,3-c]pyrrole Scaffolds from para-Quinone Methides and α-Alkylidene Succinimides.
Herein, we evolve a base-promoted synthesis of 2H-chromen-2-one and chromeno[2,3-c]pyrrole scaffolds via (4 + 2) annulation of α-alkylidene succinimides with 2-hydroxyphenyl-substituted para-quinone methides (p-QMs). Extremely selective and switchable cyclizations were obtained by modifying the base. This metal-free protocol is highlighted by its mild reaction conditions and broad substrate scope, and the viability of the existing protocol was additionally illustrated by gram-scale synthesis and further modification. Several control experiments were performed to understand the reaction mechanism.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.