Microwave-induced one-pot synthesis of 4-[3-(aryl)-1,2,4-oxadiazol-5-yl]-butan-2-ones under solvent free conditions

Freitas, Jucleiton José Rufino de; Freitas, Juliano Carlo Rufino; Silva, Ladjane P. da; Filho, João Rufino de Freitas; Kimura, Gisele Y.V.; Srivastava, Rajendra M.

doi:10.1016/j.tetlet.2007.06.116

Cited by 32 publications

(12 citation statements)

References 19 publications

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“…Observa-se que H-8 possui outra constante de acoplamento com H-7 com valor de J6 = 0,9Hz, indicando que estes hidrogênios são quimicamente equivalentes, mas magneticamente diferentes. Os dados espectroscópicos de RMN 1 H e RMN 13 C corroboram com os valores encontrados na literatura para o 1-(3-aril-1,2,4-oxadiazol-5-il) butan-2-ona descrito por Freitas et al (2007) [27].…”

Section: Figura 3: Espectros De IV Em Pastilha De Kbr Do Composto 3bunclassified

Síntese, caracterização e atividade antitumoral in vitro de uma série de 1,2,4-oxadiazois 3,5-substituídos

Silva

Acioli²,

Mata

et al. 2020

Sci. Plena

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Neste trabalho, é descrito a síntese, caracterização estrutural e atividade antitumoral in vitro de 1,2,4-oxadiazois. As arilamidoximas, produtos de partida de interesse, foram obtidos em bons rendimentos (70-92%). Por outro lado, os 3-aril-(1,2,4-oxadiazol-5-il)-propan-2-ona (5a-c) foram obtidos a partir do acetoacetato de etila com arilamidoxima através do aquecimento durante 4 horas em rendimento de 74-88%. Em seguida os compostos 3a-c foram submetidos a reação de redução com borohidreto de sódio para fornecer os 3-aril-(1,2,4-oxadiazol-5-il)-propan-2-ol (6a-c) em rendimento variando de 75-88%. Compostos contendo o núcleo oxadiazolico da série (5a-c) e (6a-c) foram submetidos a teste biológico para verificação da citoxicidade in vitro dos mesmos frente a células tumorais - HT29 (carcinoma de cólon - humano), HL60 (leucemia promielocítica) e NCI H-292 (câncer de pulmão - humano). Os compostos (5a-c) e (6a-c) tiveram suas atividades antitumoral in vitro testada e 5a/b apresentaram atividade moderada e 5c boa atividade frente as células HL60. Por outro lado, os compostos 6a-c não apresentaram atividades.

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Section: Figura 3: Espectros De IV Em Pastilha De Kbr Do Composto 3bunclassified

Síntese, caracterização e atividade antitumoral in vitro de uma série de 1,2,4-oxadiazois 3,5-substituídos

Silva

Acioli²,

Mata

et al. 2020

Sci. Plena

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“…From a synthetic point of view, amidoximes are versatile building blocks allowing the access to numerous heterocyclic compounds [23][24][25], and the formation of new C-C bonds in Suzuki [26] and Sonogashira type reactions [27]. In addition, the use of amidoximes as adsorbents and complexing agents was also described in the literature.…”

Section: Introductionmentioning

confidence: 99%

Benzamidoxime-Mediated Crotylation of Aldehydes using Potassium (Z) and (E)-Crotyltrifluoroborates

Almeida

Santos

et al. 2018

J. Mex. Chem. Soc.

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A highly diastereoselective protocol for the crotylation reaction of aldehydes using potassium (<em>Z</em>) and (<em>E</em>)-crotytrifluoroborates was developed. Benzamidoxime was employed as a renewable catalyst, which was easily recovered through a simple extraction process. This method proved to be simple, fast, regio- and chemoselective for different aldehydes. The corresponding homoallylic alcohols were obtained in good to excellent yields without the need of further purification.

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“…Among the top value‐added chemicals derived from biomass, alkyl levulinates and its derivatives have wide applications in biodiesel and fuel additives, drug blocks and green solvents, due to their excellent physical and chemical properties such as low toxicity, perfect lubricating ability, flash point stability and improved flow properties . In addition to that, alkyl levulinates could also serve as important building blocks for various chemical transformations because of its multifunctionality (a ketone group and an ester group), such as the synthesis of γ‐valerolactone (GVL), a gasoline additive admixing with low vapor pressure and high energy density .…”

Section: Introductionmentioning

confidence: 99%

HPAs and POM‐based ILs Catalyzed Effective Conversion of Furfuryl Alcohol to Alkyl Levulinate

Hao

Zhao

et al. 2017

ChemistrySelect

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Here we represented the heteropoly acids (HPAs) and polyoxometalate (POM)‐based ionic liquids (ILs) catalyzed the effective alcoholysis of furfural alcohol (FAL) to alkyl levulinate. H5AlW12O40 exhibited the highest catalytic activity among HPAs, furnishing > 99 % FAL conversion and 80 % yield of butyl levulinate (BL). The incorporation of IL framework containing sulfate group into HPAs resulted in the enhanced catalytic performance. [MIMBS]5[AlW12O40] achieved the highest BL yield of 94 % and maintained a good catalytic activity after 6 times of recycle and reuse experiments. The effect of the Hammett acidity and structure of catalyst on the catalytic performance of HPAs and POM‐based ILs was also investigated.

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Microwave-induced one-pot synthesis of 4-[3-(aryl)-1,2,4-oxadiazol-5-yl]-butan-2-ones under solvent free conditions

Cited by 32 publications

References 19 publications

Síntese, caracterização e atividade antitumoral in vitro de uma série de 1,2,4-oxadiazois 3,5-substituídos

Síntese, caracterização e atividade antitumoral in vitro de uma série de 1,2,4-oxadiazois 3,5-substituídos

Benzamidoxime-Mediated Crotylation of Aldehydes using Potassium (Z) and (E)-Crotyltrifluoroborates

HPAs and POM‐based ILs Catalyzed Effective Conversion of Furfuryl Alcohol to Alkyl Levulinate

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