Summary
Acetylation of the indazolquinones1a (6-anilino-),b (6-p-toluidino-),c (6-N-methylanilino-),g (6- or 5-methylthio-), andk (benz[f]-) by heating with acetic anhydride yields the 2-acetylindazolquinones4a, b, c, g, andk. Reductive acetylation of the quinones1c, g, h/h 1(6/5-methyl),k and — for structure elucidation — their 1-N- (2c) and 2-N- (3c, 3e)-methyl derivatives with acetic anhydride, zink powder, and sodium acetate gives the 1-acetyl-(7c, g, h/h 1,k), resp. 1-methyl- (8c), and 2-methyl- (9c, e) diacetoxyindazoles. In case of1k, two diacetyl derivatives were isolated in addition to the already known triacetyl derivative7k, regardless of the conditions chosen. Acetylation of the intermediate product of the reaction from phenylthio-benzoquinone with diazomethane also yields a triacetyl-hydroquinone (7f). UV/Vis, IR, and1H NMR spectroscopy were used for structure determination. Comparison of the UV/Vis spectra of the acetyl derivatives4 with those of1, 2, 3, and of compounds7 with those of analog substituted indazols shows that the acetyl group is located in position 2 with compounds4 and in position 1 with compounds7. By means of1H NMR spectra the position of the acetyl group can be determined by the effect of the carbonyl group on the proton in position3.
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Ott, R., Pinter, E. Untersuchungen über Chinone, 9. Mitt. Über Acetylderivate vonp-Indazolchinonen. Monatsh Chem 125, 945–954 (1994). https://doi.org/10.1007/BF00812709
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DOI: https://doi.org/10.1007/BF00812709