Catalytic IntramolecularFriedel‐Crafts Reaction of Benzyl Meldrum's Acid Derivatives: Preparation of 5,6‐Dimethoxy‐2‐Methyl‐1‐Indanone

Lou, Tiantong; Liao, E‐Ting; Wilsily, E‐Ting; Fillion, Eric

doi:10.1002/0471264229.os089.13

Cited by 2 publications

(2 citation statements)

References 3 publications

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“…Our first approach was the use of substituted malonates, protected as Meldrum's acid derivatives, as the parent compound 5 is commercially available or easily accessible on a relatively large scale ( Scheme 3 ) [ 56 ]. Therefore, we first achieved an alkylation step of 5 using a Knoevenagel reaction with benzaldehyde, followed by an in situ reduction of the resulting alkylidene [ 57 – 58 ]. Even if the reaction worked well with complete conversion, the isolation of the pure product was less straightforward and required a recrystallization from a methanol/water mixture, leading to a moderate yield (56%) due to a partial solubilization of the product 7h .…”

Section: Resultsmentioning

confidence: 99%

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

Xavier¹,

Condon²,

Gall³

et al. 2021

Beilstein J. Org. Chem.

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The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.

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Section: Resultsmentioning

confidence: 99%

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

Xavier¹,

Condon²,

Gall³

et al. 2021

Beilstein J. Org. Chem.

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“…Quaternized Meldrum’s acids 70 have been used for the synthesis of 1-indanones 71 [ 48 ]. The reaction was catalyzed by Sc(OTf) 3 and proceeded in very good yields (up to 94%) ( Scheme 24 ).…”

Section: Reviewmentioning

confidence: 99%

Synthesis of 1-indanones with a broad range of biological activity

Turek¹,

Szczęsna²,

Koprowski³

et al. 2017

Beilstein J. Org. Chem.

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This comprehensive review describes methods for the preparation of 1-indanones published in original and patent literature from 1926 to 2017. More than 100 synthetic methods utilizing carboxylic acids, esters, diesters, acid chlorides, ketones, alkynes, alcohols etc. as starting materials, have been performed. This review also covers the most important studies on the biological activity of 1-indanones and their derivatives which are potent antiviral, anti-inflammatory, analgesic, antimalarial, antibacterial and anticancer compounds. Moreover, they can be used in the treatment of neurodegenerative diseases and as effective insecticides, fungicides and herbicides.

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Catalytic IntramolecularFriedel‐Crafts Reaction of Benzyl Meldrum's Acid Derivatives: Preparation of 5,6‐Dimethoxy‐2‐Methyl‐1‐Indanone

Cited by 2 publications

References 3 publications

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

Synthesis of 1-indanones with a broad range of biological activity

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