title: Metal-free nitrative cyclization of N-aryl imines with tert-butyl nitrite: dehydrogenative access to 3-nitroindoles.
abstract: We describe here a new metal-free route for the synthesis of 3-nitroindoles by the nitrative cyclization of N-aryl imines with tert-butyl nitrite. The radical transformation allows the assembly of the indole framework through oxidative cleavage of multi C-H bonds, a nitration, cyclization and isomerization cascade.
authors.affiliation: State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China. jhli@hnu.edu.cn.
authors.forename: Guo-Bo
authors.initials: GB
authors.lastname: Deng
authors.forename: Jia-Ling
authors.initials: JL
authors.lastname: Zhang
authors.forename: Yan-Yun
authors.initials: YY
authors.lastname: Liu
authors.forename: Bang
authors.initials: B
authors.lastname: Liu
authors.forename: Xu-Heng
authors.initials: XH
authors.lastname: Yang
authors.forename: Jin-Heng
authors.initials: JH
authors.lastname: Li
mesh_terms: D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D008670:Metals; D015394:Molecular Structure; D009573:Nitrites / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry
chemical_list: D007097:Imines; D007211:Indoles; D008670:Metals; D009573:Nitrites; D009574:Nitro Compounds; C024225:n-butyl nitrite; C030374:indole