title: Facile synthesis of benzoindoles and naphthofurans through carbonaceous material-catalyzed cyclization of naphthylamines/naphthols with nitroolefins in water.
abstract: A facile and efficient approach has been established for the synthesis of benzoindole and naphthofuran derivatives via the metal-free cyclization reaction of nitroolefins with naphthylamines/naphthols. Various substituted benzoindoles and naphthofurans are obtained in good to excellent yields. Moreover, the ability to recycle the carbonaceous material makes this method quite cost-effective and environmentally benign compared to traditional acid-catalyzed methods. Theoretical studies indicated that the reaction between naphthylamine and nitroolefin catalyzed by this solid acid was thermodynamically controlled at 60 °C, resulting in the formation of the benzoindoles.
authors.affiliation: School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province 312000, China. qichenze@usx.edu.cn.
authors.forename: Furen
authors.initials: F
authors.lastname: Zhang
authors.forename: Chunmei
authors.initials: C
authors.lastname: Li
authors.forename: Chen
authors.initials: C
authors.lastname: Wang
authors.forename: Chenze
authors.initials: C
authors.lastname: Qi
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry; D014867:Water / Q000737:chemistry
chemical_list: D000475:Alkenes; D000588:Amines; D005663:Furans; D007211:Indoles; D009284:Naphthols; D009574:Nitro Compounds; D013451:Sulfonic Acids; D014867:Water; D002244:Carbon