Abstract
The treatment of N-alkyl-5-nitroindazole with stannous chloride in ethanol, aftercoupling of the obtained amines with arylsulfonyl chloride in pyridine, gave the new 4-ethoxy- and 4-chloroindazoles bearing sulfonamide in moderate to good yields. Chlorination and ethoxylation of indazole were observed during the reduction of the nitro group with anhydrous SnCl2 in ethanol. The influence of the N-alkylation in N-1 and N-2 position of 5-nitroindazole on the reduction was investigated. The presence ofethoxy group and chlorine atom at position C-4 of indazole was confirmed by x-ray diffraction analysis of compounds 7a and 8a.
Graphical Abstract
ACKNOWLEDGMENTS
We acknowledge the National Centre for Scientific and Technical Research (CNRST), Rabat, for providing the NMR and x-ray crystallography of our compounds.
SUPPLEMENTAL MATERIAL
Full characterization data, 1H and 13C NMR spectra, and x-ray crystallographic materials for this article can be accessed on the publisher’s website.