|
|||||
|
|
SnCl2/EtOH-Mediated Synthesis of Novel 4-Ethoxy- and 4-Chloroindazoles Bearing Sulfonamide Moieties |
|
| Authors: | Hakima Chicha Latifa Bouissane Lahcen El Ammari Mohamed Saadi Michel Baltas |
| Affiliation: | 1. Laboratoire de Chimie Organique et Analytiques, Faculté des Sciences et Techniques, Université Sultan Moulay Slimane, Béni-Mellal, Morocco;2. Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Rabat, Morocco;3. Université Paul Sabatier, Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique, UMR-CNRS 5068, Toulouse, France |
| Abstract: | AbstractThe 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. |
| Keywords: | Arylsulfonyl chloride N-alkyl-5-nitroindazoles N-(4-chloroindazol-5-yl)-arylsulfonamides N-(4-ethoxyindazol-5-yl)-arylsulfonamides reduction stannous chloride |