Microwave-assisted Diels–Alder reactions between Danishefsky's diene and derivatives of ethyl α-(hydroxymethyl)acrylate. Synthetic approach toward a biotinylated anti-inflammatory monocyclic cyanoenone

Zheng, Suqing; Chowdhury, Allison; Ojima, Iwao; Honda, Tadashi

doi:10.1016/j.tet.2012.12.079

Cited by 8 publications

(6 citation statements)

References 20 publications

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“…Compared to the traditional thermal conditions, the method of Zheng offers a 14-48-fold rate acceleration with serious increase in the yields. The adducts so-obtained are useful intermediates in the synthesis of a biotin conjugate of monocyclic cyanoenone with high antiinflammatory activity [98].…”

Section: Diels-alder Cycloadditionsmentioning

confidence: 99%

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Microwave-Assisted Syntheses in Organic Chemistry

Kiss

Bálint²,

Keglevich

2016

SpringerBriefs in Molecular Science

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The second part focuses on the summary of typical organic chemical reactions selected, such as coupling reactions (C-C bond formation reactions, carbon-heteroatom bond formations), condensations (aldol-type-, Claisen-, Knoevenagel reaction), multicomponent reactions (Mannich-, Biginelli-, Hantzsch-, Bucherer-Bergs-, Strecker-, Gewald-, Kabachnik-Fields-, Kindler-, Passerini-, Ugi-and domino reactions), cycloadditions (including Diels-Alder reactions). The authors tried to compile fashionable reactions that have been reviewed less in the past years.

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Section: Diels-alder Cycloadditionsmentioning

confidence: 99%

“…The [4+2] cycloaddition of 1,4-diaryl-1-aza-1,3-butadienes (98) with allenic esters at 100°C followed by a tandem 1,3-H-shift provided 1,4-dihydropyridines (100) in excellent, 83-96 % yields (Scheme 2.69). Comparative thermal reactions required 33-76 h resulting in lower yields [106].…”

Section: 4-dihydropyridinesmentioning

confidence: 99%

Microwave-Assisted Syntheses in Organic Chemistry

Kiss

Bálint²,

Keglevich

2016

SpringerBriefs in Molecular Science

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“…Zheng et al (2013) observed Diels-Alder cycloaddition between Danishefsky's diene and derivatives of ethyl α-(hydroxymethyl) acrylate, where the hydroxy group was protected, giving high yield with faster rate of reaction. These adducts are required for the synthesis of a biotin conjugate of monocyclic cyanoenone with high antiinflammatory activity.…”

Section: Diels-alder Additionmentioning

confidence: 99%

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2014

Microwave-Assisted Organic Synthesis

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“…In this context, the use of microwave (MW) irradiation in reactions is well docu-mented in the literature for their reduced reaction times, increased product yields and enhanced product purities by reducing undesired side reactions compared to conventional heating methods [13]. For this reason, microwave irradiation has been widely applied in organic synthesis in the last decades and achieved great success for many reactions, including Friedel Crafts acylation [14], Biginelli reaction in aqueous medium [15], carbon-carbon cross-coupling reactions [16], transesterification reactions [17], Diels-Alder cycloaddition [18], N-alkylation of amines [19], Hantzsch condensation [20] among many others.…”

Section: Introductionmentioning

confidence: 99%

Microwave-induced Synthesis of N-Substituted 1-Alkyl and 1-Aryl 3-Aminoisoquinolines

Méndez¹,

Villalba²,

Cánepa

et al. 2017

LOC

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Background: Aminoisoquinolines are an important class of heterocyclic compounds. These compounds present a wide range of pharmacological properties including antimalaric, anticonvulsant and anti-inflammatory. Although several preparation routes may be found in the literature for the preparation of these compounds, many of these methods present difficulties, including laborious isolation methods, drastic conditions and extended reaction times. Methods: The synthesis of N-substituted 1-alkyl and 1-aryl-3-aminoisoquinolines is developed through the reaction of 2-acylphenylacetonitriles with amines under microwave irradiation conditions. The reactions were performed in ethanol as a solvent without the use of catalyst. In parallel, these reactions were performed under identical conditions of temperature using P 2 O 5 /SiO 2 as a catalyst in different amounts. Results: A series of N-substituted 1-alkyl and 1-aryl-3-aminoisoquinolines were synthesized using microwave irradiation with as high selectivity, short reaction times and without the use of catalyst. The use of P 2 O 5 /SiO 2 as catalyst under microwave irradiation conditions was not effective for these reactions. Conclusion: The results show an efficient method for the synthesis of N-substituted 1-alkyl and 1-aryl-3-aminoisoquinolines by the reaction of 2-acylphenylacetonitriles with amines using microwave irradiation. Some important advantages for this method include a strong decrease in reaction time, a good selectivity, and the absence of catalyst, with simplicity in operation and a benefit to the environment.

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Microwave-assisted Diels–Alder reactions between Danishefsky's diene and derivatives of ethyl α-(hydroxymethyl)acrylate. Synthetic approach toward a biotinylated anti-inflammatory monocyclic cyanoenone

Cited by 8 publications

References 20 publications

Microwave-Assisted Syntheses in Organic Chemistry

Microwave-Assisted Syntheses in Organic Chemistry

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Microwave-induced Synthesis of N-Substituted 1-Alkyl and 1-Aryl 3-Aminoisoquinolines

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