title: Efficient multicomponent strategy to pentacyclic pyrazole-fused naphtho[1,8-fg]isoquinolines through cleavage of two carbon-carbon bonds.
abstract: Multicomponent reactions of acenaphthylene-1,2-dione with diaroylmethanes and electron-rich pyrazol-5-amines have been discovered. A series of new and polyfunctionalized pentacyclic pyrazole-fused naphtho[1,8-fg]isoquinolines were regioselectively synthesized. The reactions were easy to perform simply by mixing three common reactants in AcOH. During these reaction processes, the insertion of active methylene of diaroylmethane into the sp(2)-sp(2) C-C bond of the cyclohexa-2,5-dienone ring was readily achieved and two C-C bonds were cleaved under transition-metal-free conditions.
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.
authors.forename: Wen-Juan
authors.initials: WJ
authors.lastname: Hao
authors.forename: Xiao-Ping
authors.initials: XP
authors.lastname: Xu
authors.forename: Hui-Wen
authors.initials: HW
authors.lastname: Bai
authors.forename: Shun-Yi
authors.initials: SY
authors.lastname: Wang
authors.forename: Shun-Jun
authors.initials: SJ
authors.lastname: Ji
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D007546:Isoquinolines; D011720:Pyrazoles; C031280:pyrazole