Collect. Czech. Chem. Commun.
1990, 55, 1038-1048
https://doi.org/10.1135/cccc19901038
4-Aminoethylene derivatives of 2-methylbenzotriazole
Viktor Milataa, Dušan Ilavskýa, Igor Goljerb, Ján Leškob, Marc Chahinianc and Erica Henry-Baschc
a Department of Organic Chemistry, Slovak Institute of Technology, 812 37 Bratislava, Czechoslovakia
b Central Laboratory of Chemical Technique, Slovak Institute of Technology, 812 37 Bratislava, Czechoslovakia
c Laboratory of Organometallic Chemistry, University Paris-Sud, 91405 Orsay Cedex, France
Abstract
N-Methylation of 4(7)-nitrobenzotriazole (I) afforded a mixture of three isomers; one of them, 4-nitro-2-methylbenzotriazole (II) could easily be isolated. Catalytical hydrogenation of II led to the corresponding amine which in turn, afforded products of nucleophilic substitution IVa-IVi on reaction with alkoxymethylene derivatives IIIa-IIIi. Thermal cyclocondensation of IVi yielded 7-ethoxycarbonyl-6,9-dihydro-6-oxo-2-methyl-2H-triazolo[4,5-h]quinoline (V). The structure of all products was deduced from the IR, UV, 1H and 13C NMR spectral data.
