Synthesis of 4-Arylallylidenepyrazolone Derivatives
Pyrazoles and their derivatives have attracted particular attention because they have a wide variety of biological activities, and recently, we found that 4,4’-(arylmethylene)-bis-(1-phenyl-3-methyl-1<i>H</i>-pyrazole-5-ols) have good leishmanicidal activity against promastigotes of <...
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| Language: | English |
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MDPI AG
2021-11-01
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| Series: | Chemistry Proceedings |
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| Online Access: | https://www.mdpi.com/2673-4583/8/1/7 |
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| author | Esteban Aguilar-Llanos Juan Carlos Romero-Benavides Jorge Heredia-Moya |
| author_facet | Esteban Aguilar-Llanos Juan Carlos Romero-Benavides Jorge Heredia-Moya |
| author_sort | Esteban Aguilar-Llanos |
| collection | DOAJ |
| description | Pyrazoles and their derivatives have attracted particular attention because they have a wide variety of biological activities, and recently, we found that 4,4’-(arylmethylene)-bis-(1-phenyl-3-methyl-1<i>H</i>-pyrazole-5-ols) have good leishmanicidal activity against promastigotes of <i>Leishmania mexicana.</i> 4-Arylidenepyrazolone derivatives also have antiparasitic activity and are intermediates in the synthesis of these bispirazoles that are formed by the equimolar reaction of 3-methyl-1-phenyl-2-pyrazoline-5-one with aromatic aldehydes. In order to obtain new compounds with potential leishmanicidal activity, we attempted to synthesize several 4-arylallylidenepyrazolone derivatives through the reaction of pyrazol-3-one with different cinnamaldehydes. We report here the study of the synthesis of some 4-arylallylidenepyrazolone derivatives from the reaction between 5-methyl-2-phenyl-2,4-dihydro-3<i>H</i>-pyrazol-3-one and 4-nitrocinnamaldehyde. We found that <i>L</i>-proline and FeCl<i><sub>3</sub></i> were the best catalysts, and we also observed a solvent effect in the reaction. Our preliminary results indicate that aprotic solvents favor the formation of the 2<i>Z</i> isomer instead of the 2<i>E</i> isomer. |
| first_indexed | 2024-03-11T06:46:59Z |
| format | Article |
| id | doaj.art-ba04479c6df34b25a9817ff8c2d4cd33 |
| institution | Directory Open Access Journal |
| issn | 2673-4583 |
| language | English |
| last_indexed | 2024-03-11T06:46:59Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry Proceedings |
| spelling | doaj.art-ba04479c6df34b25a9817ff8c2d4cd332023-11-17T10:18:13ZengMDPI AGChemistry Proceedings2673-45832021-11-0181710.3390/ecsoc-25-11714Synthesis of 4-Arylallylidenepyrazolone DerivativesEsteban Aguilar-Llanos0Juan Carlos Romero-Benavides1Jorge Heredia-Moya2Facultad de Ciencias Químicas, Universidad Central del Ecuador, Quito 1705727, EcuadorDepartamento de Química, Universidad Técnica Particular de Loja, Loja 1101608, EcuadorCentro de Investigación Biomédica (CENBIO), Facultad de Ciencias de la Salud Eugenio Espejo, Universidad UTE, Quito 1705727, EcuadorPyrazoles and their derivatives have attracted particular attention because they have a wide variety of biological activities, and recently, we found that 4,4’-(arylmethylene)-bis-(1-phenyl-3-methyl-1<i>H</i>-pyrazole-5-ols) have good leishmanicidal activity against promastigotes of <i>Leishmania mexicana.</i> 4-Arylidenepyrazolone derivatives also have antiparasitic activity and are intermediates in the synthesis of these bispirazoles that are formed by the equimolar reaction of 3-methyl-1-phenyl-2-pyrazoline-5-one with aromatic aldehydes. In order to obtain new compounds with potential leishmanicidal activity, we attempted to synthesize several 4-arylallylidenepyrazolone derivatives through the reaction of pyrazol-3-one with different cinnamaldehydes. We report here the study of the synthesis of some 4-arylallylidenepyrazolone derivatives from the reaction between 5-methyl-2-phenyl-2,4-dihydro-3<i>H</i>-pyrazol-3-one and 4-nitrocinnamaldehyde. We found that <i>L</i>-proline and FeCl<i><sub>3</sub></i> were the best catalysts, and we also observed a solvent effect in the reaction. Our preliminary results indicate that aprotic solvents favor the formation of the 2<i>Z</i> isomer instead of the 2<i>E</i> isomer.https://www.mdpi.com/2673-4583/8/1/7pyrazoles4-arylallylidenepyrazolonescinnamaldehydesvalence isomerization |
| spellingShingle | Esteban Aguilar-Llanos Juan Carlos Romero-Benavides Jorge Heredia-Moya Synthesis of 4-Arylallylidenepyrazolone Derivatives Chemistry Proceedings pyrazoles 4-arylallylidenepyrazolones cinnamaldehydes valence isomerization |
| title | Synthesis of 4-Arylallylidenepyrazolone Derivatives |
| title_full | Synthesis of 4-Arylallylidenepyrazolone Derivatives |
| title_fullStr | Synthesis of 4-Arylallylidenepyrazolone Derivatives |
| title_full_unstemmed | Synthesis of 4-Arylallylidenepyrazolone Derivatives |
| title_short | Synthesis of 4-Arylallylidenepyrazolone Derivatives |
| title_sort | synthesis of 4 arylallylidenepyrazolone derivatives |
| topic | pyrazoles 4-arylallylidenepyrazolones cinnamaldehydes valence isomerization |
| url | https://www.mdpi.com/2673-4583/8/1/7 |
| work_keys_str_mv | AT estebanaguilarllanos synthesisof4arylallylidenepyrazolonederivatives AT juancarlosromerobenavides synthesisof4arylallylidenepyrazolonederivatives AT jorgeherediamoya synthesisof4arylallylidenepyrazolonederivatives |