Microwave accelerated solvent-free synthesis of flavanones

Sagrera, Gabriel; Seoane, Gustavo

doi:10.1590/s0103-50532005000500026

Cited by 31 publications

(20 citation statements)

References 14 publications

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“…Moreover, 4 and 8 were submitted to two different conditions of reaction (AcOH and AcONa/AcOH) to afford the same flavanone (11). [22] Flavone 12 was produced by heating at 130°C the mixture of 4 and I 2 in DMSO (Scheme 2). [23] The structures of these compounds were confirmed by using their spectroscopic and spectrometric data (Supporting information).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Functionalized 1‐Aryl‐3‐phenylthiazolylpropanoids and Their Potential as Anticancer Agents

et al. 2020

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Natural products have inspired the development of multipletarget anticancer agents. To reach this goal, preparation of hybrid molecules was adopted as a recent approach to target and affect both sensitive and resistant cells. In the continuation of the search for potent anticancer agents, nine thiazole-based chalcones were prepared. Their cytotoxic activities were evaluated against twenty cancer cell lines and against the normal cell line AML12 hepatocytes. The key steps of these syntheses involved Hantzsch, Sommelet, and Claisen-Schmidt reactions. Julia-Colonna reaction was used to achieve the epoxidation of the double bond. The products were purified by chromatographic techniques and were characterized by spectroscopic methods. Cytotoxicity assays were performed by rezasurin reduction test. Compounds 4-10 showed promising cytotoxic activities. 4 and 7 were the most cytotoxic with IC 50 values lower than 1 μM against seven and two cancer cell lines, respectively. This study disclosed a new series of potential anticancer agents among which 4 and 7 deserve further investigation to develop drug for sensitive and multidrug resistant (MDR) cancer.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Functionalized 1‐Aryl‐3‐phenylthiazolylpropanoids and Their Potential as Anticancer Agents

et al. 2020

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“…This reaction can be performed using acidic or basic as catalyst and heat, microwave as well as light as the energy source [4,[7][8][16][17]. The acid-catalyzed cyclication can be carried out by refluxing the chalcone in acetic acid or ethanol, in the presence of sulfuric or phosphoric acid.…”

Section: Figmentioning

confidence: 99%

“…In this research, conversion of chalcone into flavanone was conducted in basic condition using NaOAc catalyst due to the corrosive property of the acid. The conversion of chalcone into flavanone is slow reaction, thus heat or light is needed to accelerate the reaction [17]. Additionally, the heat also might break the hydrogen bond between hydroxy and carbonyl groups.…”

Section: Figmentioning

confidence: 99%

Synthesis of Flavanone-6-Carboxylic Acid Derivatives From Salicylic Acid Derivative

et al. 2012

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Synthesis of flavanone-6-carboxylic acid derivatives had been conducted via the route of chalcone. The synthesis was carried out from salicylic acid derivative, via esterification, Fries rearrangement, Keywords: Flavanone-6-carboxylic acid; Fries rearrangement; Claisen-Schmidt condensation; 1,4-nucleophilic addition ABSTRAK Sintesis turunan flavanon-6-asam karboksilat melalui senyawa antara kalkon telah dilakukan. Sintesis dilakukan dari bahan dasar asam 4-hidroksibenzoat melalui reaksi esterifikasi, penataan ulang Fries, kondensasi Claisen-Schmidt and adisi 1,4-nukleofilik. Elusidasi struktur dari produk dilakukan menggunakan spektrometer IR, 1 H-NMR, GC-MS dan UV-Vis. Reaksi asam 4-hidroksibenzoat dengan metanol terkatalisis asam sulfat menghasilkan metil 4-hidroksibenzoat (87%). Asetilasi terkatalisis asam terhadap produk esterifikasi menggunakan asam asetat anhidrida menghasilkan metil 4-asetoksibenzoat (75% yield). Selanjutnya, penataan ulang Fries metil 4-asetoksibenzoat dengan katalis AlCl 3 menghasilkan turunan asetofenon berupa asam 3-asetil-4-hidroksibenzoat (67%

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“…12, 2011 microwave irradiation in "dry media" reducing substantially the reaction times and increasing product yields. [24][25][26] Because of the advantages that microwave irradiation has over conventional reflux methods, we present, herein, the Knoevenagel synthesis of 3-arylacrylonitriles by the reaction of 2-(benzo[d]thiazol-2-yl)acetonitrile with different substituted arylaldehydes. The synthesis has been assisted by microwave irradiation and under solventfree conditions.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis under solvent-free conditions of (E)-2-(Benzo[d]thiazol-2-yl)-3-arylacrylonitriles

Trilleras¹,

Velásquez²,

Pacheco³

et al. 2011

J. Braz. Chem. Soc.

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Uma série de (E)-2-(benzo[d]tiazol-2-il)-3-arilacrilonitrilas foi sintetizada pela condensação de Knoevenagel assistida por microondas, na ausência de solvente, partindo do correspondente 2-(benzo[d]tiazo-2-il)acetonitrila e aldeídos aromáticos, contendo tanto grupos doadores de elétrons, como retiradores. Os tempos de reação foram consideravelmente curtos e os produtos, obtidos em rendimentos moderados (50-75%) e boa pureza. A configuração da dupla ligação da acrilonitrila não pôde ser estabelecida por métodos comuns de RMN. No entanto, estudos teóricos sugerem que nesses compostos o isômero E é mais estável do que o Z, o que está de acordo com algumas evidências experimentais.A series of (E)-2-(benzo[d]thiazol-2-yl)-3-arylacrylonitriles was synthesized by microwave assisted Knoevenagel condensation under solvent-free conditions from the corresponding 2-(benzo[d]thiazol-2-yl)acetonitrile and aromatic aldehydes with electrondonating/electronwithdrawing groups. The reaction times were considerably short and the products obtained in moderate yields (50 to 75%) and good purity. The configuration of the acrylonitrile double bond could not be established by regular NMR methods. However, theoretical studies suggest that the E isomer is more stable than Z, which is in good agreement with some experimental evidences.

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Microwave accelerated solvent-free synthesis of flavanones

Cited by 31 publications

References 14 publications

Synthesis of Functionalized 1‐Aryl‐3‐phenylthiazolylpropanoids and Their Potential as Anticancer Agents

Synthesis of Functionalized 1‐Aryl‐3‐phenylthiazolylpropanoids and Their Potential as Anticancer Agents

Synthesis of Flavanone-6-Carboxylic Acid Derivatives From Salicylic Acid Derivative

Microwave-assisted synthesis under solvent-free conditions of (E)-2-(Benzo[d]thiazol-2-yl)-3-arylacrylonitriles

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