title: Cyclization and N-iodosuccinimide-induced electrophilic iodocyclization of 3-aza-1,5-enynes to synthesize 1,2-dihydropyridines and 3-iodo-1,2-dihydropyridines.
abstract: Metal-free cyclization and N-iodosuccinimide-induced electrophilic iodocyclization of readily available 3-aza-1,5-enynes have been developed. The reactions selectively give 1,2-dihydropyridines and 3-iodo-1,2-dihydropyridines involving an aza-Claisen rearrangement and a 6π-electrocyclization step. Furthermore, the reaction could be carried out in 10 g scale for the synthesis of 1,2-dihydropyridines.
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China.
authors.forename: Xiaoyi
authors.initials: X
authors.lastname: Xin
authors.forename: Dongping
authors.initials: D
authors.lastname: Wang
authors.forename: Fan
authors.initials: F
authors.lastname: Wu
authors.forename: Xincheng
authors.initials: X
authors.lastname: Li
authors.forename: Boshun
authors.initials: B
authors.lastname: Wan
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013388:Succinimides / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001372:Aza Compounds; D004095:Dihydropyridines; D013388:Succinimides; C008155:N-iodosuccinimide