Synthesis of N-cycloalkenylazoles.
N-(1-Cycloalkenyl)pyrroles 3a,b, -pyrazoles 6a,b, and -imidazoles 9a,b were synthesized via elimination of benzotriazole or 5-phenyltetrazole from the corresponding 1-[1-(heterocycyl)cycloalkyl]benzotriazoles 2, 5, and 8 or 1-[1-(heterocycyl)cyclohexyl]-5-phenyltetrazole (12 and 14). Intermediates 2, 5, 8, 12 and 14 were obtained by cyclizations of dihaloalkanes with N-(benzotriazol-1-ylmethyl)heterocycles, 1-imidazol-1-ylmethyl-5-phenyltetrazole (11), or 1-pyrazol-1-ylmethyl-5-phenyltetrazole (13) in the presence of n-BuLi.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
Maimait
Rexiat
R
Xu
Yong-Jiang
YJ
Gyoung
Young Soo
YS
D001393:Azoles / Q000138:chemical synthesis*; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis; D007093:Imidazoles / Q000138:chemical synthesis; D009474:Neurons; D011720:Pyrazoles / Q000138:chemical synthesis; D011758:Pyrroles / Q000138:chemical synthesis; D014947:Wounds and Injuries
D001393:Azoles; D006574:Heterocyclic Compounds, 2-Ring; D006575:Heterocyclic Compounds, 3-Ring; D007093:Imidazoles; D011720:Pyrazoles; D011758:Pyrroles