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Studies on synthetic approaches to 1H- and 2H-indazolyl derivatives. 2001

E M Isin, and M de Jonge, and N Castagnoli
Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, USA.

Synthetic approaches designed to provide 1H- and 2H-indazolyl derivatives of potential biological interest are reported. Special emphasis has been placed on the characterization of indazolylpyridinium products generated from reactions between indazole and 4-chloro-1-methylpyridinium iodide under various conditions. A stable mixture consisting of 3 parts of the 1H-isomer 9 to 1 part of the 2H-isomer 10 was obtained at room temperature in the presence of the base 2,2,6,6-tetramethylpiperidine (TMP). The same reaction at 60 degrees C gave only the 1H-isomer 9. At 100 degrees C in the absence of TMP only the 2H-isomer 10 was formed. The isomerization of 10 to 9 was found to proceed quantitatively at 60 degrees C but only in the presence of TMP. The effects of temperature and base on the course of these reactions are rationalized in terms of kinetic and thermodynamic parameters.

UI MeSH Term Description Entries
D007191 Indazoles A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES. Indazole
D013057 Spectrum Analysis The measurement of the amplitude of the components of a complex waveform throughout the frequency range of the waveform. (McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed) Spectroscopy,Analysis, Spectrum,Spectrometry
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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