Methods for the Synthesis of Hydrazinopyridines and Some of Their Characteristics

Abstract

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Synthesis of Hydrazinylpyridines via Nucleophilic Aromatic Substitution and Further Transformation to Bicyclo[2.2.2]octenes Fused with Two N-Aminosuccinimide Moieties

“…[9][10][11][12] Hydrazinyl group in hydrazinylpyridines can be substituted with a hydrogen, halogen, hydroxy, or phenyl group or reduced to an amine group. 5 2-Hydrazinylpyridine can be used for the synthesis of organo-metallic complexes applied as antibiotics, 13,14 as a complexing site for technetium in molecules used in radioactive imaging in medicine, 15 and as a precursor in the synthesis of some pesticides. 5,16 Both 2-and 4-hydrazinylpyridines can be used in the synthesis of compounds that exhibit antitumor activity 17,18 and antidepressant characteristics.…”

“…Hydrazinylpyridines can be also prepared via nucleophilic aromatic substitution of a halogen in halopyridines with hydrazine (Scheme 1), 5 appropriate halogens being fluorine, chlorine, and bromine. 5 Besides hydrazine hydrate, substituted hydrazines can also be used, for example, methylhydrazine 28 and 4-tolylhydrazine. 29 Substitution most easily occurs on activated ortho-and para-positions regarding the nitrogen of pyridine ring, but can be in some cases achieved even on meta-position.…”

“…34,35 Pyridine ring is activated for the nucleophilic substitution if other electron-withdrawing substituents (nitro, cyano group) are present. 5 Examples of such compounds are 2chloro-3-nitropyridine, 28 2-bromo-5-chloro-3-nitropyridine, 28…”

“…Hydrazinylpyridines and their substituted analogues are simple organic molecules that can be used for many further transformations: acting as nucleophiles, [2][3][4][5] for the synthesis of more complex nitrogen heterocyclic compounds, mainly various [1,2,3]triazolopyridines [5][6][7] and azaindazoles, 8 or for hydrazone formation. 5 Hydrazine and its substituted analogues can be furthermore used for the synthesis of pyrazole and its derivatives. [9][10][11][12] Hydrazinyl group in hydrazinylpyridines can be substituted with a hydrogen, halogen, hydroxy, or phenyl group or reduced to an amine group.…”

“…5 2-Hydrazinylpyridine can be used for the synthesis of organo-metallic complexes applied as antibiotics, 13,14 as a complexing site for technetium in molecules used in radioactive imaging in medicine, 15 and as a precursor in the synthesis of some pesticides. 5,16 Both 2-and 4-hydrazinylpyridines can be used in the synthesis of compounds that exhibit antitumor activity 17,18 and antidepressant characteristics. 19 Hydrazide derivatives of pyrimidine are used as precursors for the synthesis of various compounds of pharmacological interest.…”