Edson de Oliveira Lima Filho , Raquel Nery Simão , Marcela Cristina Pereira de Barros , Guilherme Pereira Guedes , Vitor Francisco Ferreira , Fernando de Carvalho da Silva
{"title":"Stoichiometry-controlled chemoselective mechanochemical indolation of 1,2-naphthoquinones under metal- and solvent-free conditions","authors":"Edson de Oliveira Lima Filho , Raquel Nery Simão , Marcela Cristina Pereira de Barros , Guilherme Pereira Guedes , Vitor Francisco Ferreira , Fernando de Carvalho da Silva","doi":"10.1016/j.tet.2025.134917","DOIUrl":null,"url":null,"abstract":"<div><div>In this study, we report the development of a novel methodology for the synthesis of stoichiometry-controlled chemoselective of fifteen (mono or tris)-indole-naphthalen(di)one derivatives by mechanochemical indolation of 1,2-naphthoquinone. The reactions were conducted under solvent-free conditions using the mechanochemical technique. Notably, the method enables selective control over the formation of both symmetric and non-symmetric trisubstituted products.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"187 ","pages":"Article 134917"},"PeriodicalIF":2.2000,"publicationDate":"2025-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402025004739","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
In this study, we report the development of a novel methodology for the synthesis of stoichiometry-controlled chemoselective of fifteen (mono or tris)-indole-naphthalen(di)one derivatives by mechanochemical indolation of 1,2-naphthoquinone. The reactions were conducted under solvent-free conditions using the mechanochemical technique. Notably, the method enables selective control over the formation of both symmetric and non-symmetric trisubstituted products.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.