Condensation of monosubstituted isopropylidene malonates with Mannich bases

Jacobs, Robert T.; Wright, Allen D.; Smith, F.

doi:10.1021/jo00140a038

Cited by 16 publications

(3 citation statements)

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“…HR73 was synthesized starting from Phenylmeldrum's acid and 6-bromo-1-dimethylaminomethyl-2-naphthol as described [61]. Identity and purity were assured by mass, infrared, and NMR spectroscopy as well as by elemental analysis.…”

Section: Methodsmentioning

confidence: 99%

SIRT1 Regulates HIV Transcription via Tat Deacetylation

et al. 2005

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The human immunodeficiency virus (HIV) Tat protein is acetylated by the transcriptional coactivator p300, a necessary step in Tat-mediated transactivation. We report here that Tat is deacetylated by human sirtuin 1 (SIRT1), a nicotinamide adenine dinucleotide-dependent class III protein deacetylase in vitro and in vivo. Tat and SIRT1 coimmunoprecipitate and synergistically activate the HIV promoter. Conversely, knockdown of SIRT1 via small interfering RNAs or treatment with a novel small molecule inhibitor of the SIRT1 deacetylase activity inhibit Tat-mediated transactivation of the HIV long terminal repeat. Tat transactivation is defective in SIRT1-null mouse embryonic fibroblasts and can be rescued by expression of SIRT1. These results support a model in which cycles of Tat acetylation and deacetylation regulate HIV transcription. SIRT1 recycles Tat to its unacetylated form and acts as a transcriptional coactivator during Tat transactivation.

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Section: Methodsmentioning

confidence: 99%

SIRT1 Regulates HIV Transcription via Tat Deacetylation

et al. 2005

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“…In recent years, the preparation of 5-alkenyl-1,3-dioxane-4,6-diones has attracted strong interest owing to the broad spectrum of their properties: these compounds can be employed as versatile intermediates for a series of natural products and heterocyclic compounds with potentially biological activity [1][2][3][4][5]. In addition, it is also reacted with Grignard reagent in conjugate addition [6] or conjugated dienes in Diels-Alder cycloaddition [7].…”

Section: Introductionmentioning

confidence: 99%

Solvent-Free Synthesis of 5-Alkenyl-2,2-butylidene-1, 3-dioxane-4,6-diones under Ultrasonic Irradiation with o-Phthalimide-N-Sulfonic Acid as Catalyst

Lin¹,

Xu²,

Liao³

2013

IJOC

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5-Alkenyl-2,2-butylidene-1,3-dioxane-4,6-diones were synthesized by the Knoevenagel condensation reaction of aromatic aldehydes with 2,2-butylidene-1,3-dioxane-4,6-dione using o-phthalimide-N-sulfonic acid as catalyst, without solvent under ultrasonic irradiation. The present method has some notable advantages such as mild reaction conditions, short reaction times, less catalyst dosage and high yields with the green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be reused for five times without any noticeable decrease in the catalytic activity.

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“…Meldrum's acid and its 5-substituted derivatives are versatile synthons in organic synthesis , (ii) Michael-type additions of Meldrum's acid to electrophilic olefins 8,12 or to their equivalents; , (iii) palladium-catalyzed coupling reaction between allyl derivatives (allylic halides and esters) and Meldrum's acid. ,,, As part of our ongoing research, we need to develop a mild method to C -dialkylate Meldrum's acid directly using alcohols as alkylating agents. For this purpose, the Mitsunobu dehydrative alkylation appears to offer the best promise.…”

Section: Introductionmentioning

confidence: 99%

Mitsunobu C-Alkylation of Meldrum's Acids

Shing¹,

Narkunan

1997

J. Org. Chem.

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C-Dialkylation of Meldrum's acid (2a) and 5-benzyl Meldrum's acid (2b) can be achieved through Mitsunobu dehydration using allylic and arylmethyl alcohols as alkylating agents. This is the first time that the Mitsunobu reaction is successfully applied to the C-alkylation of a highly enolizable cyclic β-dicarbonyl system. With primary (allylic and arylmethyl) alcohols, the alkylations always take place at the carbon bearing the hydroxy group. For secondary allylic alcohols, a catalytic amount of Pd(0) must be added to enhance the regioselectivity of C-alkylation over O-alkylation. With (Ph3P)4Pd(0) as a catalyst, the reaction occurs specifically at the less hindered carbon, and the configuration of the resultant double bond is always trans. Attempts to monoalkylate Meldrum's acids 2a and 2b failed.

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Condensation of monosubstituted isopropylidene malonates with Mannich bases

Cited by 16 publications

References 1 publication

SIRT1 Regulates HIV Transcription via Tat Deacetylation

SIRT1 Regulates HIV Transcription via Tat Deacetylation

Solvent-Free Synthesis of 5-Alkenyl-2,2-butylidene-1, 3-dioxane-4,6-diones under Ultrasonic Irradiation with o-Phthalimide-N-Sulfonic Acid as Catalyst

Mitsunobu C-Alkylation of Meldrum's Acids

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