title: Cascade nitration/cyclization of 1,7-enynes with tBuONO and H2O: one-pot self-assembly of pyrrolo[4,3,2-de]quinolinones.
abstract: Here we describe the one-pot construction of the pyrrolo[4,3,2-de]quinolinone scaffold by a cascade nitration/cyclization sequence of 1,7-enynes with tBuONO and H2O. The cascade proceeds through alkene nitration, 1,7-enyne 6-exo-trig cyclization, C-H nitrations, and redox cyclization, and exhibits excellent functional group tolerance. The mechanism was investigated using in situ high-resolution mass spectrometry (HR-MS).
authors.affiliation: State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China).
authors.forename: Yu
authors.initials: Y
authors.lastname: Liu
authors.forename: Jia-Ling
authors.initials: JL
authors.lastname: Zhang
authors.forename: Ren-Jie
authors.initials: RJ
authors.lastname: Song
authors.forename: Peng-Cheng
authors.initials: PC
authors.lastname: Qian
authors.forename: Jin-Heng
authors.initials: JH
authors.lastname: Li
mesh_terms: D003500:Cyclization; D009566:Nitrates / Q000737:chemistry*; D015363:Quinolones / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D009566:Nitrates; D015363:Quinolones; D014867:Water
keywords: cascade reactions; cyclization; enynes; nitration; nitrogen heterocycles