Reaction of (Z)-1-aryl-3-hexen-1,5-diynes with sodium azide: synthesis of 1-aryl-1H-benzotriazoles.
[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.
Chen
Zhong-Yi
ZY
Faculty of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung, Taiwan.
Wu
Ming-Jung
MJ
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*
D000475:Alkenes; D007202:Indicators and Reagents; D014230:Triazoles; D019810:Sodium Azide; D004121:Dimethyl Sulfoxide