Meldrum’s acid and related compounds in the synthesis of natural products and analogs

Ivanov, Andrey S.

doi:10.1039/b716020h

Cited by 169 publications

(67 citation statements)

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“…[5][6][7] The structural simplicity of Meldrum's acid (1), combined with its unique properties, has made this a versatile reagent in organic syntheses, especially those based on the multicomponent process. [8][9][10] In addition, the design and development of environment-friendly catalysts have been the subject of intense research. 11 The hydrotalcite like compounds (HT), also known as layered double hydroxides (LDH), are anionic clay materials that have been extensively investigated as heterogeneous base catalysts.…”

Section: Introductionmentioning

confidence: 99%

New Multicomponent Reaction for the Direct Synthesis of β-Aryl-γ-nitroesters Promoted by Hydrotalcite-Derived Mixed Oxides as Heterogeneous Catalyst

D'Oca

Naciuk

Silva

et al. 2016

Journal of the Brazilian Chemical Society

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A new approach based on multicomponent/domino combined reactions for the synthesis of γ-nitroesters promoted by a mixed aluminium-magnesium oxides derived from hydrotalcite-like material was developed. Different γ-nitroesters were synthesized in 15-95% yield using Meldrum's acid, aromatic aldehydes, nitromethane and different alcohols as reagents and solvents. The γ-aminobutyric acid derivatives, Phenibut and Baclofen, were prepared in 63 and 61% overall yield, respectively, through a two steps synthetic strategy. A mechanistic pathway was proposed based on the gas chromatography mass spectrometry (GC-MS) and electrospray ionization mass spectrometry (ESI-MS) experiments.

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Section: Introductionmentioning

confidence: 99%

New Multicomponent Reaction for the Direct Synthesis of β-Aryl-γ-nitroesters Promoted by Hydrotalcite-Derived Mixed Oxides as Heterogeneous Catalyst

D'Oca

Naciuk

Silva

et al. 2016

Journal of the Brazilian Chemical Society

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“…Domino reactions [1][2][3] are considered to be versatile synthetic tools and are used for the synthesis of structurally diverse compounds including biologically active natural products and drugs. [2][3][4][5] As a strong CH-acid, Meldrum's acid readily enters into condensation reactions of the aldol 6 and Knoevenagel 3,7 type to yield 5-alkenyl-2,2-dimethyl-1,3-dioxane-4,6-diones which are widely used in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

“…[2][3][4][5] As a strong CH-acid, Meldrum's acid readily enters into condensation reactions of the aldol 6 and Knoevenagel 3,7 type to yield 5-alkenyl-2,2-dimethyl-1,3-dioxane-4,6-diones which are widely used in organic synthesis. With a vast number of diverse synthetic applications Meldrum's acid may be considered a unique synthon.…”

Section: Introductionmentioning

confidence: 99%

“…With a vast number of diverse synthetic applications Meldrum's acid may be considered a unique synthon. Its methylidene derivatives, for instance, often are engaged as intermediates in multicomponent reactions (MCR) in which the Meldrum's acid moiety decomposes 2,3,[12][13][14] as it is the case with intra-and intermolecular Friedel-Crafts C-alkylations 15 and NH-acylations of thioamides.…”

Section: Introductionmentioning

confidence: 99%

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Domino Knoevenagel/Michael addition/C-acylation reaction. Synthesis of 1,3-cyclohexane-1,3-diones

Jagodziński¹,

Westerlich²

2010

Arkivoc

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The three component reactions of Meldrum's acid, 1,3-bis-(benzotriazol-1-yl)propan-2-one or 1-benzotriazol-1-ylpropan-2-one and an aldehyde, carried out in DMF at 60 ºC gave rise to 2,4-bis-(benzotriazol-1-yl)cyclohexane-1,3-diones or 4-benzotriazol-1-ylcyclohexane-1,3-diones, respectively, in fairly high yields. Unlike similar reactions reported earlier with acetone, the reactions with 1,3-bis-(benzotriazol-1-yl)propan-2-one and 1-benzotriazol-1-ylpropan-2-one proceeded via an intramolecular acylation of the other methyl group of acetone.

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“…1 Monoalkylated derivatives 1 are synthesized from Meldrum's acid 3 by condensation with aldehyde 2 (or by acylation 3 ) followed by hydrogenation.…”

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confidence: 99%

5-Alkyl and 5,5-Dialkyl Meldrum’s Acids

Mieriņa

2013

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research spotlight Introduction 5-Alkyl and 5,5-dialkyl Meldrum's acids (1 and 2, respectively) are used in total synthesis. 1 Monoalkylated derivatives 1 are synthesized from Meldrum's acid 3 by condensation with aldehyde 2 (or by acylation 3 ) followed by hydrogenation. 5-Alkyl and 5,5-Dialkyl Meldrum's Acids5,5-Dialkyl Meldrum's acids 2 can be obtained by alkylation of Meldrum's acid 3 or its monoalkylated derivatives 1 (Scheme 1). 4 Herein, reactions of Meldrum's acids 1 and 2 proceeding with destruction of 1,3-dioxane cycle are reviewed.(A) Hydrolysis of Meldrum's acid 2 leads to malonic or acetic acid derivatives. 5 Radical reduction of compound 2 with SmI 2 and H 2 O forms 3-hydroxypropanoic acids 4 selectively. The first step is activation of Meldrum's acid via coordination of SmI 2 to the carbonyl group, followed by electron transfer. 6 (B) Detz et al. 7 have reported that dimethyl malonate 5 can be obtained from propargylic derivative 2. The authors propose that the first step of the reaction cascade is copper-mediated addition of Meldrum's acid 2 to the triple bond and sequential methanolysis of the dioxane cycle forming lactone 6, which is further cleaved with methoxide leading to compound 5.(C) β-Substituted aldehydes 7 can be synthesized by Lewis base promoted hydrosilylation of Meldrum's acids 1 with phenylsilane, followed by hydrolysis. In situ treatment of aldehyde 7 with an amine and sequential hydrogenation of the formed imine with H 2 in the presence of Pd/C or with NaBH(OAc) 3 gives γ-substituted amines 8. 8 (D) 5-Alkyl Meldrum's acids 1 are used for the rapid synthesis of 2-alkyl acrylates 9 via Mannich-type reactions. The advantage of the method is the clean conversion into products due to the formation of volatile by-products -acetone, carbon dioxide, and dimethylamine. 9

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Meldrum’s acid and related compounds in the synthesis of natural products and analogs

Abstract: This critical review focuses on applications of Meldrum's acid and its derivatives to the synthesis of natural products and analogs. It covers all relevant literature from 1991 to August 2007 (181 references).

Cited by 169 publications

References 170 publications

New Multicomponent Reaction for the Direct Synthesis of β-Aryl-γ-nitroesters Promoted by Hydrotalcite-Derived Mixed Oxides as Heterogeneous Catalyst

New Multicomponent Reaction for the Direct Synthesis of β-Aryl-γ-nitroesters Promoted by Hydrotalcite-Derived Mixed Oxides as Heterogeneous Catalyst

Domino Knoevenagel/Michael addition/C-acylation reaction. Synthesis of 1,3-cyclohexane-1,3-diones

5-Alkyl and 5,5-Dialkyl Meldrum’s Acids

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