Design, synthesis, and structure of alkyl 1H-pyrazolecarboxylates from a raspberry ketone methyl ether

This paper reports a one-pot synthesis of 5-[2-(4-methoxyphenyl)ethyl]-1 H -pyrazole-3-carboxylates via cyclocondensation of 1,1,1-trichloro-4-methoxy-6-(4-methoxyphenyl)hex-3-en-2-one with hydrazine hydrochloride in ROH (R = Me, Et, n -Pr, i -Pr, i -Bu, i -Am, hexadecyl) under conventional and micr...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-10, Vol.56 (10), p.1314-1320
Main Authors: Goulart, Taís B., Neves, Adriana M., Soares, Mayara S. P., Stefanello, Francieli M., Campos, Patrick T., Moura, Sidnei, Cargnelutti, Roberta, Flores, Alex F. C.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
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Summary:This paper reports a one-pot synthesis of 5-[2-(4-methoxyphenyl)ethyl]-1 H -pyrazole-3-carboxylates via cyclocondensation of 1,1,1-trichloro-4-methoxy-6-(4-methoxyphenyl)hex-3-en-2-one with hydrazine hydrochloride in ROH (R = Me, Et, n -Pr, i -Pr, i -Bu, i -Am, hexadecyl) under conventional and microwave heating. Yields are comparable in both methods, but under MW heating the reaction proceeds faster. The antioxidant activity of the compounds was measured using DPPH radical scavenging assay. It was observed, that the increase of the alcohol chain length decreases the antioxidant potential of the raspberry ketone derived molecular system.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-020-02816-z