Oxidation ofN-Aminophthalimide in the Presence of Conjugated Azoalkenes: Azimines, Azoaziridines, and [1,2,3]Triazoles
作者:Mikhail A. Kuznetsov、Ljudmila M. Kuznetsova、Joachim G. Schantl、Klaus Wurst
DOI:10.1002/1099-0690(200104)2001:7<1309::aid-ejoc1309>3.0.co;2-h
日期:2001.4
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].