title: Annulation Reaction of 3-Acylmethylidene Oxindoles with Huisgen Zwitterions and Its Applications in the Syntheses of Pyrrolo[4,3,2-de]quinolinones and Marine Alkaloids Ammosamides.
abstract: A novel annulation reaction of 3-acylmethylidene oxindoles with Huisgen zwitterions is unveiled that leads to an unprecedented synthetic method for complex pyrrolo[4,3,2-de]quinolinones and marine alkaloids ammosamides A-C. This method features simplicity, high efficiency, and broad substrate scope and is accordingly anticipated to significantly facilitate the preparation and bioassay of the relevant pyrroloquinoline alkaloids and their analogues.
authors.affiliation: The State Key Laboratory of Elemento-Organic Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, P. R. China.
authors.forename: Changjiang
authors.initials: C
authors.lastname: Yang
authors.affiliation: The State Key Laboratory of Elemento-Organic Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, P. R. China.
authors.forename: Xiangyu
authors.initials: X
authors.lastname: Chen
authors.affiliation: The State Key Laboratory of Elemento-Organic Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, P. R. China.
authors.forename: Tong
authors.initials: T
authors.lastname: Tang
authors.affiliation: The State Key Laboratory of Elemento-Organic Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, P. R. China.
authors.forename: Zhengjie
authors.initials: Z
authors.lastname: He
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D000577:Amides; D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification*; D006575:Heterocyclic Compounds, 3-Ring; D007211:Indoles / Q000737:chemistry*; D008386:Marine Biology; D015394:Molecular Structure; D000078183:Oxindoles; D011758:Pyrroles / Q000737:chemistry / Q000302:isolation & purification*; D011804:Quinolines / Q000737:chemistry*; D015363:Quinolones / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000470:Alkaloids; D000577:Amides; D001688:Biological Products; D006575:Heterocyclic Compounds, 3-Ring; D007211:Indoles; D000078183:Oxindoles; D011758:Pyrroles; D011804:Quinolines; D015363:Quinolones; C534622:ammosamide A; C534623:ammosamide B; C549633:ammosamide C; C410406:pyrroloquinoline; C022960:2-oxindole