title: Divergent synthesis of 2,3-dihydro-1H-pyrroles, 3-alkyl-1H-pyrroles and 3-alkenyl-1H-pyrroles from 2,4-pentadienenitriles and isocyanides.
abstract: An efficient and divergent one-pot synthesis of 2,3-dihydro-1H-pyrroles, 3-alkyl-1H-pyrroles and 3-alkenyl-1H-pyrroles from readily accessible 2,4-pentadienenitriles with isocyanide based on reaction condition selection has been described. The reaction of 2,4-pentadienenitriles with ethyl isocyanoacetate undergoes a formal [2 + 3] annulation either to generate 2,3-dihydro-1H-pyrroles in the presence of DBU (0.3 equiv.) in EtOH at room temperature or to give 3-alkyl-1H-pyrroles in the presence of DBU (2.0 equiv.) in EtOH under reflux. Moreover, the 2,3-dihydro-1H-pyrroles could be converted to 3-alkenyl-1H-pyrroles with DDQ as an oxidant.
authors.affiliation: Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. China. yjliang@ciac.ac.cn dwdong@ciac.ac.cn.
authors.forename: Xiaoqing
authors.initials: X
authors.lastname: Xin
authors.forename: Xu
authors.initials: X
authors.lastname: Liu
authors.forename: Dingyuan
authors.initials: D
authors.lastname: Zhang
authors.forename: Rui
authors.initials: R
authors.lastname: Zhang
authors.forename: Yongjiu
authors.initials: Y
authors.lastname: Liang
authors.forename: Fushe
authors.initials: F
authors.lastname: Han
authors.forename: Dewen
authors.initials: D
authors.lastname: Dong
mesh_terms: D000085:Acetates / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D003486:Cyanides / Q000138:chemical synthesis* / Q000737:chemistry; D004583:Electrons; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000085:Acetates; D000475:Alkenes; D003486:Cyanides; D009570:Nitriles; D011758:Pyrroles; C007659:ethyl cyanoacetate