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Pyrazolo[3,4‐ e ] [1,4] thiazepines: Synthesis and structure proof
Author(s) -
Swett Leo R.,
Ratajczyk James D.,
Nordeen Carl W.,
Aynilian George H.
Publication year - 1975
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570120611
Subject(s) - chemistry , sodium hydride , methyl iodide , dimethylformamide , hydrolysis , yield (engineering) , sulfur , sodium iodide , flue gas desulfurization , medicinal chemistry , organic chemistry , materials science , solvent , metallurgy
Pyrazolo[3,4‐ e ][1,4]thiazepine derivatives were obtained by reacting 5‐amino‐1,3‐dimethylpyrazole with arylaldehydes or ketones and mercaptoacetic acid. The structure proof of these derivatives was carried out by identifying the benzylpyrazole products obtained by desulfurization and subsequent hydrolysis, and by comparison of the spectral data of a series of analogous pyrazolothiazepines. Treating the pyrazolothiazepines with sodium hydride and methyl iodide in dimethylformamide or dimethylsulfoxide resulted in a ring contraction with the elimination of sulfur, to yield the pyrazolopyridones in addition to the N ‐methylpyrazolothiazepines.