2-Pyrones. XV. Substituted 3-Cinnamoyl-4-hydroxy-6-methyl-2-pyrones from Dehydroacetic Acid

Wiley, Richard H.; Jarboe, Charles H.; H, Ellert

doi:10.1021/ja01624a045

Cited by 48 publications

(19 citation statements)

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“…The simplest of 2,6-disubstituted-4H-pyran-4-ones is 2,6-dimethyl-4H-pyran-4-one (compound 2 in Fig.2), which is obtained in 86% yield from dehydroacetic acid (compound 1 in Fig.2) by acidic rearrangement with following decarboxylation (see Fig.2) [32][33]. Figure 2.…”

Section: Synthesis Of the Backbone Fragment: 26-disubstituted-4h-pyrmentioning

confidence: 99%

“…One of oldest, but no less important methods known for the synthesis of 2,6-disubstituted-4H-pyran-4-ones is to obtain them from 3-substituted-vinylcarbonyl-4-hydroxy-6-methyl-2H-pyran-2-ones (compounds 17 in Fig.6) [33]. Compounds 17 are obtained from dehydroacetic acid (compound 1 in Fig.6), in which the methyl group in the acetyl fragment is activated to react preferentially with aromatic aldehydes (see Fig.6) giving 3-substitutedvinylcarbonyl-4-hydroxy-6-methyl-2H-pyran-2-ones (compounds 17 in Fig.6) [33,36].…”

mentioning

confidence: 99%

“…Compounds 17 are obtained from dehydroacetic acid (compound 1 in Fig.6), in which the methyl group in the acetyl fragment is activated to react preferentially with aromatic aldehydes (see Fig.6) giving 3-substitutedvinylcarbonyl-4-hydroxy-6-methyl-2H-pyran-2-ones (compounds 17 in Fig.6) [33,36]. Details on the obtained compounds 17 and their dependence on substituents (R) in their molecules are given in Table 1.…”

mentioning

confidence: 99%

“…Using this approach it is possible to obtain many different mono-styryl-substituted 4H-pyran-4-ones (compounds 17 in Fig.7). However only a few of previously synthesized compounds 17 give 2-styryl-substituted-6-methyl-4H-pyran-4-ones (compounds 18 in Fig.7) by acidic decarboxylation under the reaction conditions reported in [30,33] (see Fig.7) as summarised in Table 2 Yield -the practical production of the particular compound 17 in the reaction of dehydroacetic acid (compound 1 in Fig.6) with the corresponding aromatic aldehyde. M.p.…”

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confidence: 99%

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Synthesis and Physical Properties of Red Luminescent Glass Forming Pyranylidene and Isophorene Fragment Containing Derivatives

Zariņš¹,

Vembris²,

Kokars³

et al. 2012

Organic Light Emitting Devices

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Section: Synthesis Of the Backbone Fragment: 26-disubstituted-4h-pyrmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Synthesis and Physical Properties of Red Luminescent Glass Forming Pyranylidene and Isophorene Fragment Containing Derivatives

Zariņš¹,

Vembris²,

Kokars³

et al. 2012

Organic Light Emitting Devices

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“…3-Cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-ones and their vinylogs depicted in scheme 1 have been prepared under reaction conditions described ealier [11].…”

Section: General Procedures For Preparation Of I-ximentioning

confidence: 99%

Structure and spectal properties of cinnamoyl pyrones and their vinylogs

Tykhanov¹,

Serikova²,

Yaremenko³

et al. 2010

Open Chemistry

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Abstract:The 1 H-NMR and quantum chemical analysis of the stability of tautomers of cinnamoyl pyrone derivatives and vinylogs has been studied. The relationship between the structure of the most stable tautomer and its spectral properties has been investigated. It has been determined that the tautomer of highest stability (88-100 molar %) has an α-pyrone structure and exhibits a trans-conformation in the cinnamoyl fragment. An intense fluorescence of dyes has been observed in non-polar solvents with cinnamoyl fragments having electron-donating substituents or several double bonds in the polymethine chain. A gradient in solvent polarity resulted in fluorescence quenching which permits the use of the dyes as intensometric fluorometric probes for medium polarity examination. Sp. z o.o. © Versita

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The Aldol Condensation

Nielsen

Houlihan²

2011

Organic Reactions

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The aldol condensation takes its name from aldol (3‐hydroxybutanal) a name introduced by Wurtz who first prepared the beta‐hydroxy aldehyde from acetaldehdye in 1872. The aldol condensation includes reactions producing beta‐hydroxy aldehydes or beta‐hydroxy ketones by self condensations or mixed condensations of aldehydes and ketones as well as reactions leading to alpha, beta‐unsaturated aldehydes or alpha,beta‐unsaturated ketones formed by dehydration of intermediate beta‐aldols or beta‐ketals. The Claisen‐Schmidt condensation is most often taken to be the condensation of an aromatic aldehyde or ketone usually in the presence of a basic catalyst. The term aldol condensation has also been applied to many other condensations involving the reaction of an aldehyde or ketone. These condenations are discussed. The present review includes examples that are solely condensation reactions of aldehydes and ketones.

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2-Pyrones. XV. Substituted 3-Cinnamoyl-4-hydroxy-6-methyl-2-pyrones from Dehydroacetic Acid

Cited by 48 publications

References 0 publications

Synthesis and Physical Properties of Red Luminescent Glass Forming Pyranylidene and Isophorene Fragment Containing Derivatives

Synthesis and Physical Properties of Red Luminescent Glass Forming Pyranylidene and Isophorene Fragment Containing Derivatives

Structure and spectal properties of cinnamoyl pyrones and their vinylogs

The Aldol Condensation

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