Regiospecificity of nucleophilic substitution in 4, 6-dinitro-1-phenyl-1H-indazole

AM Starosotnikov, AV Lobach, VV Kachala…

Index: Starosotnikov; Lobach; Kachala; Shevelev Russian Chemical Bulletin, 2004 , vol. 53, # 3 p. 584 - 587

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Citation Number: 10

Abstract

Abstract The reactions of 4, 6-dinitro-1-phenyl-1 H-indazole with anionic nucleophiles RS– and N 3–lead to the regiospecific replacement of the nitro group at position 4. The reaction with N 2 H 4· H 2 O+ FeCl 3 also results in reduction of only the 4-NO 2 group. Based on this fact, a procedure was developed for the preparation of previously unknown 3-unsubstituted 4-X-6-nitro-1-phenyl-1 H-indazoles (X is a residue of a nucleophile or NH 2). Comparison ...