SYNTHESES BASED ON 4-CHLORO-1-[3,5-DI(TRIFLUOROMETHYL)PHENYL]-, 4-CHLORO-1-(2,4-DIFLUOROPHENYL)-5-FORMYL-3-METHYL-6,7-DIHYDROINDAZOLES, AND 4-CHLORO-5-FORMYL-3-METHYL-1-(2-PYRIDYL)-6,7-DIHYDROINDAZOLES
DOI:
https://doi.org/10.1007/8304Keywords:
β-arylaminovinyl ketones, β-arylaminovinylarylimines, 4, 5-dihydro-7H-benzo[b]indazolo[4, 5-e]diazepines, 5-dihydro-1H-pyrazolo[3, 4-e]indazoles, 3, 8-substituted 4, 5-dihydropyrazolo[5, 4-h]quinazolines, β-chlorovinylaldehydesAbstract
Vilsmeier formylation of 1-[3,5-di(trifluoromethyl)phenyl]- and 1-(2,4-difluorophenyl)-3-methyl-4-oxo-4,5,6,7-tetrahydroindazoles gave the corresponding 1-aryl-4-chloro-5-formyl-3-methyl-6,7-dihydroindazoles. Reaction of the latter with amidines, o-phenylenediamine, hydrazine, or hydroxylamine gave a series of 1-aryl-3-methyl-6,6-dihydroindazoles annelated at positions 4 and 5. The reaction of 4-chloro-5-formyl-3-methyl-1-(2-pyridyl)-6,7-dihydroindazole with substituted anilines gave 5-arylaminomethylene-4-oxo- or 5-arylaminomethylene-4-arylimino-3-methyl-1-(2-pyridyl)-4,5,6,7-tetrahydroindazoles depending on the molar ratio of reagents and the nucleophilicity of the amines.How to Cite
Strakova, I.; Strakovs, A.; Petrova, M. Chem. Heterocycl. Compd. 2005, 41, 637. [Khim. Geterotsikl. Soedin. 2005, 740.]
For this article in the English edition, see DOI 10.1007/s10593-005-0196-2
