{"title":"离子液体催化的生物质衍生烷基乳酸酯环化反应:生物活性二氢喹喔啉和喹喔啉的时间依赖性可调合成","authors":"Shanshan Liu, Zhenzhen Li, Pingjun Zhang, Yaoyao Zhang, Weiwei Dong, Lin-Yu Jiao","doi":"10.1021/acssuschemeng.4c05755","DOIUrl":null,"url":null,"abstract":"Recyclable ionic liquid–catalyzed tandem annulation of alkyl lactates has been demonstrated, enabling divergent synthesis of dihydroquinoxalines and quinoxalines as a function of reaction time. Notably, dihydroquinoxalines could be furnished swiftly at room temperature with high yields. More significantly, the tunable synthesis is exemplified by repeatably stopping–restarting processes. Furthermore, biological studies indicate that dihydroquinoxalines with alkoxycarbonyl substitution at the C4 position are promising agrochemical candidates in terms of their antifungal activity. This method features the advantages of biomass utilization (RP > 75%), eco-benign manner (E-factor < 3), and the capacity for antileishmanial agent synthesis. Mechanistic studies established a kinetic preference for the formation of dihydroquinoxaline rather than quinoxaline through decarboxylation being thermodynamically favored. The current study reveals that reaction time could modulate the selective conversion of lactates and demonstrates the feasibility of the production of biologically valuable heterocycles from biomass.","PeriodicalId":25,"journal":{"name":"ACS Sustainable Chemistry & Engineering","volume":null,"pages":null},"PeriodicalIF":7.1000,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Ionic Liquid–Catalyzed Annulation of Biomass-Derived Alkyl Lactates: Time-Dependent Tunable Synthesis of Bioactive Dihydroquinoxalines and Quinoxalines\",\"authors\":\"Shanshan Liu, Zhenzhen Li, Pingjun Zhang, Yaoyao Zhang, Weiwei Dong, Lin-Yu Jiao\",\"doi\":\"10.1021/acssuschemeng.4c05755\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Recyclable ionic liquid–catalyzed tandem annulation of alkyl lactates has been demonstrated, enabling divergent synthesis of dihydroquinoxalines and quinoxalines as a function of reaction time. Notably, dihydroquinoxalines could be furnished swiftly at room temperature with high yields. More significantly, the tunable synthesis is exemplified by repeatably stopping–restarting processes. Furthermore, biological studies indicate that dihydroquinoxalines with alkoxycarbonyl substitution at the C4 position are promising agrochemical candidates in terms of their antifungal activity. This method features the advantages of biomass utilization (RP > 75%), eco-benign manner (E-factor < 3), and the capacity for antileishmanial agent synthesis. Mechanistic studies established a kinetic preference for the formation of dihydroquinoxaline rather than quinoxaline through decarboxylation being thermodynamically favored. The current study reveals that reaction time could modulate the selective conversion of lactates and demonstrates the feasibility of the production of biologically valuable heterocycles from biomass.\",\"PeriodicalId\":25,\"journal\":{\"name\":\"ACS Sustainable Chemistry & Engineering\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":7.1000,\"publicationDate\":\"2024-10-29\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Sustainable Chemistry & Engineering\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acssuschemeng.4c05755\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Sustainable Chemistry & Engineering","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acssuschemeng.4c05755","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Ionic Liquid–Catalyzed Annulation of Biomass-Derived Alkyl Lactates: Time-Dependent Tunable Synthesis of Bioactive Dihydroquinoxalines and Quinoxalines
Recyclable ionic liquid–catalyzed tandem annulation of alkyl lactates has been demonstrated, enabling divergent synthesis of dihydroquinoxalines and quinoxalines as a function of reaction time. Notably, dihydroquinoxalines could be furnished swiftly at room temperature with high yields. More significantly, the tunable synthesis is exemplified by repeatably stopping–restarting processes. Furthermore, biological studies indicate that dihydroquinoxalines with alkoxycarbonyl substitution at the C4 position are promising agrochemical candidates in terms of their antifungal activity. This method features the advantages of biomass utilization (RP > 75%), eco-benign manner (E-factor < 3), and the capacity for antileishmanial agent synthesis. Mechanistic studies established a kinetic preference for the formation of dihydroquinoxaline rather than quinoxaline through decarboxylation being thermodynamically favored. The current study reveals that reaction time could modulate the selective conversion of lactates and demonstrates the feasibility of the production of biologically valuable heterocycles from biomass.
期刊介绍:
ACS Sustainable Chemistry & Engineering is a prestigious weekly peer-reviewed scientific journal published by the American Chemical Society. Dedicated to advancing the principles of green chemistry and green engineering, it covers a wide array of research topics including green chemistry, green engineering, biomass, alternative energy, and life cycle assessment.
The journal welcomes submissions in various formats, including Letters, Articles, Features, and Perspectives (Reviews), that address the challenges of sustainability in the chemical enterprise and contribute to the advancement of sustainable practices. Join us in shaping the future of sustainable chemistry and engineering.