title: Efficient synthesis of maleimides and carbazoles via Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters.
abstract: Lewis acid Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.
authors.affiliation: Laboratory of Chemical Genomics, Shenzhen Graduate School, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Peking University, Beijing 100871, China.
authors.forename: Yuanzhen
authors.initials: Y
authors.lastname: Li
authors.forename: Haixia
authors.initials: H
authors.lastname: Zou
authors.forename: Jianxian
authors.initials: J
authors.lastname: Gong
authors.forename: Jing
authors.initials: J
authors.lastname: Xiang
authors.forename: Tuoping
authors.initials: T
authors.lastname: Luo
authors.forename: Junmin
authors.initials: J
authors.lastname: Quan
authors.forename: Guoxin
authors.initials: G
authors.lastname: Wang
authors.forename: Zhen
authors.initials: Z
authors.lastname: Yang
mesh_terms: D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004952:Esters / Q000737:chemistry*; D008301:Maleimides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010770:Phosphotransferases / Q000037:antagonists & inhibitors / Q000378:metabolism; D000067856:Poly(ADP-ribose) Polymerase Inhibitors; D011065:Poly(ADP-ribose) Polymerases / Q000378:metabolism; D017967:Zinc Compounds / Q000737:chemistry*
chemical_list: D002227:Carbazoles; D004791:Enzyme Inhibitors; D004952:Esters; D008301:Maleimides; D009570:Nitriles; D000067856:Poly(ADP-ribose) Polymerase Inhibitors; D017967:Zinc Compounds; D011065:Poly(ADP-ribose) Polymerases; D010770:Phosphotransferases