caa a22 4500 605530629 CHVBK 20210128100824.0 cr unu---uuuuu 210128e20150501xx s 000 0 eng 10.1134/S1070428015050115 doi (NATIONALLICENCE)springer-10.1134/S1070428015050115 Synthesis and transformations of perfluoroalkyl-containing 6,7-dihydro-1 H -indazol-4(5 H )-ones oximes [Elektronische Daten] [T. Khlebnikova, Yu. Piven', A. Baranovskii, F. Lakhvich] Refluxing 3-perfluoroalkyl-6,7-dihydro-1H-indazol-4(5H)-ones with 4-fold excess of hydroxylamine hydrochloride in pyridine afforded their (E)-oximes. The obtained oximes were alkylated with ethyl iodide and acylated with carboxylic acids chlorides to obtain (E)-O-alkyl- and (E)-O-acyloximes respectively. Heating oximes in PPA at 120°C results in their aromatization by Semmler-Wolff reaction, hydrolysis of perfluoroalkyl groups, and generation of 4-amino-1-aryl-5,6-dimethyl-1H-indazole-3-carboxylic acids from of 3-tri-fluoromethylindazolone oximes and 1-(4-amino-1-aryl-5,6-dimethyl-1H-indazol-3-yl)-fluoroalkan-1-ones from of 3-perfluoroethyl- and 3-perfluoropropylindazolone oximes. Pleiades Publishing, Ltd., 2015 Khlebnikova T. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus aut Piven' Yu Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus aut Baranovskii A. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus aut Lakhvich F. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus aut Russian Journal of Organic Chemistry Pleiades Publishing 51/5(2015-05-01), 650-656 1070-4280 51:5<650 2015 51 11178 https://doi.org/10.1134/S1070428015050115 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1134/S1070428015050115 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Khlebnikova T. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus aut NATIONALLICENCE 700 1- Piven' Yu Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus aut NATIONALLICENCE 700 1- Baranovskii A. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus aut NATIONALLICENCE 700 1- Lakhvich F. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus aut NATIONALLICENCE 773 0- Russian Journal of Organic Chemistry Pleiades Publishing 51/5(2015-05-01), 650-656 1070-4280 51:5<650 2015 51 11178