Synthesis of hybrid compounds by benzylation of acylhydrazones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

N -Benzylation of acylhydrazones of the hydroxybenzaldehyde series with 3,5-di- tert -butyl-4-hydroxybenzyl acetate was performed at room temperature in the absence of acid or base catalysts. Carboxamides do not react with 3,5-di- tert -butyl-4-hydroxybenzyl acetate under similar conditions. N-Benzy...

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Bibliographic Details
Published in:Russian chemical bulletin 2021-10, Vol.70 (10), p.1964-1972
Main Authors: Bukharov, S. V., Bakhdyrova, D. F., Tagasheva, R. G., Burilov, A. R., Litvinov, I. A., Chachkov, D. V., Vereshchagina, Ya. A.
Format: Article
Language:English
Subjects:
Acetic acid
Aromatic compounds
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Hydrazones
Hydroxybenzaldehydes
Inorganic Chemistry
Isomers
Organic Chemistry
Phenols
Room temperature
Synthesis
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Summary:N -Benzylation of acylhydrazones of the hydroxybenzaldehyde series with 3,5-di- tert -butyl-4-hydroxybenzyl acetate was performed at room temperature in the absence of acid or base catalysts. Carboxamides do not react with 3,5-di- tert -butyl-4-hydroxybenzyl acetate under similar conditions. N-Benzylation of isoniazid and (diphenylphosphoryl)acetic acid hydrazones was shown to be an efficient method for the synthesis of new hybrid compounds containing moieties of biologically active acylhydrazones and sterically hindered phenols. N -Benzyl derivatives of isoniazid and (diphenylphosphoryl)acetic acid hydrazones containing a hydroxy group at the ortho position of the aromatic ring are formed as individual E isomers with respect to the C-N double bond.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-021-3304-2