title: FeCl3-mediated three-component cascade reaction: an effective approach to the construction of highly functionalized pyrrolo[1,2-c]quinazolinones.
abstract: An unexpected FeCl3-mediated three-component cascade reaction has been used to construct structurally diverse pyrrolo[1,2-c]quinazolinone derivatives with potential biological activities. This method has advantages of mild conditions, simple work-up, as well as wide substrate scope, which makes it a powerful approach to the synthesis of diverse pyrrolo[1,2-c]quinazolinones. This cascade reaction involves 1,3-dipolar cycloaddition between azomethine ylides and allenoates, followed by intramolecular nucleophilic addition in the presence of FeCl3. The obtained products could be easily transformed into derivatives with the pyrrolo[2,3-c]quinazoline alkaloid skeleton.
authors.affiliation: Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (P.R. China).
authors.forename: Hu-Fei
authors.initials: HF
authors.lastname: Zheng
authors.forename: Zhi-Hua
authors.initials: ZH
authors.lastname: Yu
authors.forename: Wei
authors.initials: W
authors.lastname: Yuan
authors.forename: Zi-Long
authors.initials: ZL
authors.lastname: Tang
authors.forename: John
authors.initials: J
authors.lastname: Clough
authors.forename: Yu-Cheng
authors.initials: YC
authors.lastname: Gu
authors.forename: De-Qing
authors.initials: DQ
authors.lastname: Shi
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry; D061565:Cycloaddition Reaction; D007501:Iron / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D052999:Quinazolinones / Q000138:chemical synthesis* / Q000737:chemistry; D013882:Thiosemicarbazones / Q000737:chemistry
chemical_list: D000470:Alkaloids; D001391:Azo Compounds; D011758:Pyrroles; D052999:Quinazolinones; D013882:Thiosemicarbazones; C512188:azomethine; D007501:Iron
keywords: allenes; azo compounds; domino reactions; fused-ring systems; iron