title: Reaction of (Z)-1-aryl-3-hexen-1,5-diynes with sodium azide: synthesis of 1-aryl-1H-benzotriazoles.
abstract: [reaction: see text] A novel tandem cascade reaction involving 1,3-dipolar cycloaddition reaction, anionic cyclization, and sigmatropic rearrangement for the synthesis of 1-aryl-1H-benzotriazoles 2 and 3 was accomplished by treatment of the (Z)-1-aryl-3-henen-1,5-diynes (1) with sodium azide in DMF or DMSO at 80 degrees C for 12 h and gives 65-91% yields.
authors.affiliation: Faculty of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung, Taiwan.
authors.forename: Zhong-Yi
authors.initials: ZY
authors.lastname: Chen
authors.forename: Ming-Jung
authors.initials: MJ
authors.lastname: Wu
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis*; D003500:Cyclization; D004121:Dimethyl Sulfoxide; D007202:Indicators and Reagents; D008958:Models, Molecular; D019810:Sodium Azide / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis*
chemical_list: D000475:Alkenes; D007202:Indicators and Reagents; D014230:Triazoles; D019810:Sodium Azide; D004121:Dimethyl Sulfoxide