title: Multicomponent Coupling Cyclization Access to Cinnolines via in Situ Generated Diazene with Arynes, and α-Bromo Ketones.
abstract: A transition-metal-free multicomponent coupling cyclization reaction was explored involving arynes, tosylhydrazine, and α-bromo ketones. The reaction proceeds via a formal [2 + 2 + 2] cycloaddition, giving access to cinnoline derivatives in moderate yields under mild conditions. Three chemical bonds were formed-two C-N bonds and one C-C bond-in a single step.
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University , Hubei, Wuhan 430079, P. R. China.
authors.forename: Wen-Ming
authors.initials: WM
authors.lastname: Shu
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University , Hubei, Wuhan 430079, P. R. China.
authors.forename: Jun-Rui
authors.initials: JR
authors.lastname: Ma
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University , Hubei, Wuhan 430079, P. R. China.
authors.forename: Kai-Lu
authors.initials: KL
authors.lastname: Zheng
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University , Hubei, Wuhan 430079, P. R. China.
authors.forename: An-Xin
authors.initials: AX
authors.lastname: Wu
mesh_terms: D002384:Catalysis; D003500:Cyclization; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D007094:Imides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006574:Heterocyclic Compounds, 2-Ring; D006842:Hydrocarbons, Brominated; D007094:Imides; D007659:Ketones; C038867:diazene; C476282:cinnoline