New Heterocyclic Precursors for Thermal Generation of Reactive, Electron-Rich 1,2-Diaza-1,3-butadienes
作者:Robert K. Boeckman,、Ping Ge、Jessica E. Reed
DOI:10.1021/ol0165645
日期:2001.11.1
[reaction--see text] [corrected] The preparation and thermolysis of new stable heterocyclic precursors of 1,2-diaza-1,3-butadienes is described. The resulting reactive diazadienes are trapped in situ with N-phenylmaleimide [corrected]. The effect of precursor structure on the temperature at which the diazadienes are generated is discussed.
The oxidation of N-aminophthalimide (1) with lead tetraacetate in the presence of the phenylazoalkenes 2 afforded 2-phenylazo-1-(N-phthalimido)aziridines 3 or 2- phenyl[1,2,3]triazoles 7, as well as phthalimide (4). The reaction of 2-phenylazo-1-propene (2d) produced 5-methyl-2-phenyl-[1,2,3]triazole (7d) and N-[2-(phenylhydrazono)propylidene-amino]phthalimide (8d). The cyclic azoalkene 3,3,5-trimethyl-3H-pyrazole (11) gave a mixture of (Z)-3,3,5-trimethyl-[N-(phthalimido)amino]-3H-pyrazol-1-ium-2N-ide [(Z)-12] together with the regioisomers (E)- and (Z)-3,3,5-trimethyl-1-[N-(phthalimido)amino]-3H-pyrazol-2-ium-1N-ides [(E)- and (Z)-13].
SCHANTL, J. G.;HEBEISEN, P.;KARPELLUS, P., SYNTH. COMMUN., 19,(1989) N-2, C. 39-48
作者:SCHANTL, J. G.、HEBEISEN, P.、KARPELLUS, P.
DOI:——
日期:——
SCHANTL, J. G.;KARPELLUS, P.;PREAN, M., TETRAHEDRON, 1982, 38, N 17, 2643-2652