{"title":"Visible-Light-Driven Synthesis of Pyrrolo[3,4-b]quinolin-1-one Imines Exhibiting Aggregation-Induced Enhanced Emission.","authors":"Chinnagounder Kameshwaran, Fazlur-Rahman Nawaz Khan","doi":"10.1002/asia.202500770","DOIUrl":null,"url":null,"abstract":"<p><p>In recent years, visible light-mediated transformations have gained significant attention. In this work, we report the synthesis of N-substituted 2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-ones via a one-pot strategy involving C(sp<sup>3</sup>)-H functionalization, cyclization, and condensation to form the corresponding imines under visible-light conditions. Furthermore, the imines exhibited Aggregation-Induced Enhanced Emission (AIEE) properties and favorable photophysical response toward metal ions. Subsequent metal-free aerobic oxidation of these imines in the presence of a peroxide medium afforded the corresponding amides. The synthetic utility of this protocol was further demonstrated through post-functionalization of the products and gram-scale synthesis.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":" ","pages":"e00770"},"PeriodicalIF":3.3000,"publicationDate":"2025-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1002/asia.202500770","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
In recent years, visible light-mediated transformations have gained significant attention. In this work, we report the synthesis of N-substituted 2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-ones via a one-pot strategy involving C(sp3)-H functionalization, cyclization, and condensation to form the corresponding imines under visible-light conditions. Furthermore, the imines exhibited Aggregation-Induced Enhanced Emission (AIEE) properties and favorable photophysical response toward metal ions. Subsequent metal-free aerobic oxidation of these imines in the presence of a peroxide medium afforded the corresponding amides. The synthetic utility of this protocol was further demonstrated through post-functionalization of the products and gram-scale synthesis.
期刊介绍:
Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics.
Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews.
A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal.
Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).