26663-56-9Relevant academic research and scientific papers
Synthesis and Properties of 4H-Imidazoles. Part 2.
Moody, Christopher J.,Rees, Charles W.,Young, Richard G.
, p. 335 - 339 (2007/10/02)
The 1-(2,2-disubstituted alk-1-enyl)-5-phenyltetrazoles 2 and 4 are prepared from 1-methyl-5-phenyltetrazole and 5-phenyl-1-trimethylsilylmethyltetrazole by formation and appropriate interception of the α-lithioalkyl derivatives.Photolysis of the tetrazoles 2a and 4 gives the stable 4H-imidazoles 9 and 5, respectively.Similar photolysis of the tetrazole 2b gives the tetrazolophenanthrene 12 by an oxidative photocyclisation which is faster than nitrogen extrusion from the tetrazole ring.However, on further irradiation the tetrazolophenanthrene 12 can be transformed into the polycyclic 4H-imidazole 13.The 4H-imidazoles all undergo alkyl or aryl shifts to carbon when heated, 5,7,9 and 13 giving 6,8,10 and 14 respectively.
Synthesis of Imidazoles from Alkenes
Casey, Michael,Moody, Christopher J.,Rees, Charles W.
, p. 1933 - 1941 (2007/10/02)
Alkenes are converted into imidazoles through their epoxides by a sequence involving ring-opening with readily available 2-tributylstannyltetrazoles (8), dehydration of the resulting alcohols (9) using methyltriphenoxyphosphonium iodide in a improved procedure to give 1-alkenyltetrazoles (12), which give imidazoles (17) on photolysis.
A New Synthesis of Imidazoles
Casey, Michael,Moody, Christopher J.,Rees, Charles W.
, p. 714 - 715 (2007/10/02)
Alkenes are converted into imidazoles through their epoxides by treatment with 2-tri-n-butylstannyltetrazoles (2), followed by dehydration with methyltriphenoxyphosphonium iodide in an improved procedure, and photolysis of the resulting vinyltetrazoles (4).
