title: NIS/PhI(OAc)2-mediated diamination/oxidation of N-alkenyl formamidines: facile synthesis of fused tricyclic ureas.
abstract: Facile synthesis of bicyclic ureas by NIS/PhI(OAc)2-mediated diamination/oxidation of N-alkenyl formamidines is reported. Bulky aromatic groups such as 2,6-diisopropylphenyl and mesityl and alkyl groups were tolerated towards the process. Several control experiments have been performed, and the reaction outcomes indicate that the oxidation process is probably concerted with the diamination cyclization, and succinimide generated from NIS-mediated aminoamidiniumation step promoted the PhI(OAc)2-mediated oxidation step. The new methodology provides an efficient method for the synthesis of fused tricyclic ureas.
authors: Key Laboratory for Advanced Materials; Institute of Fine Chemicals, School of Chemistry&Molecular Engineering, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237 (China). zhangj@ecust.edu.cn.
authors: Jun
authors: J
authors: Zhang
authors: Weijie
authors: W
authors: Wu
authors: Xuejun
authors: X
authors: Zhang
authors: Gengtao
authors: G
authors: Zhang
authors: Sheng
authors: S
authors: Xu
authors: Min
authors: M
authors: Shi
mesh_terms: D000578:Amidines / Q000737:chemistry*; D002384:Catalysis; D019295:Computational Biology; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
chemical_list: D000578:Amidines; D011083:Polycyclic Compounds; D014508:Urea
keywords: N-iodosuccinimide; alkenes; aminoamidiniumation; deamination; oxidation