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

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

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2004, Volume: 53, Number: 3, Pages: 584-587 Pages count : 4 DOI: 10.1023/b:rucb.0000035642.41056.81

Authors

Starosotnikov A.M. ¹ , Lobach A.V. ¹ , Kachala V.V. ¹ , Shevelev S.A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation

The reactions of 4,6-dinitro-1-phenyl-1H-indazole with anionic nucleophiles RS– and N3 – lead to the regiospecific replacement of the nitro group at position 4. The reaction with N2H4·H2O + FeCl3 also results in reduction of only the 4-NO2 group. Based on this fact, a procedure was developed for the preparation of previously unknown 3-unsubstituted 4-X-6-nitro-1-phenyl-1H-indazoles (X is a residue of a nucleophile or NH2). Comparison of the data on the selective nucleophilic substitution (4-NO2 group) in 3-Z-1-aryl-4,6-dinitro-1H-indazoles shows that in the case of Z = H, the regiospecificity of substitution is determined by the electronic effect of the annelated pyrazole ring.

Starosotnikov A.M. , Lobach A.V. , Kachala V.V. , Shevelev S.A.
Regiospecificity of nucleophilic substitution in 4,6-dinitro-1-phenyl-1H-indazole
Russian Chemical Bulletin. 2004. V.53. N3. P.584-587. DOI: 10.1023/b:rucb.0000035642.41056.81 WOS Scopus OpenAlex

Web of science:	WOS:000223566500013
Scopus:	2-s2.0-4043074218
OpenAlex:	W2950010896

DB	Citing
OpenAlex	16
Scopus	18
Web of science	26