Concise Synthesis of Guanidine-Containing Heterocycles Using the Biginelli Reaction

Nilsson, Bradley L.; Overman, Larry E.

doi:10.1021/jo061199m

Cited by 92 publications

(44 citation statements)

References 55 publications

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“…DHPMs represent a heterocyclic system of remarkable pharmacological and therapeutic properties such as antiviral, antibacterial, and antitumor [5][6][7]. Several alkaloids-derivate DHPMs possessing biological and anti-HIV characters have been isolated from marine sources [8][9][10]. There is an inherent stereogenic center in DHPMs, and individual enantiomer is found to exhibit different or opposite pharmaceutical activities [11,12].…”

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confidence: 99%

Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid

Lu¹,

Chen²,

Zhang³

et al. 2011

Int J of Quantum Chemistry

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In this study, enantioselective Biginelli reaction of aldehyde, b-ketoester, and urea catalyzed by natural (2R, 3R)-tartaric acid has been investigated using density functional theory calculations. The results indicate that the most favorable pathway involves a protonated imine from aldehyde and urea in the first step. Tartaric acid forms H-bonds network with substrates enhancing the electrophilicity of protonated imine and the nucleophilicity of b-ketoester. (R)-3,4-Dihydropyrimidin-2-(1H)-ones is preferable for the reaction. The solvent effect is discussed in the prediction of enantiomeric excess (ee) values in ethanol and water.

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confidence: 99%

Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid

Lu¹,

Chen²,

Zhang³

et al. 2011

Int J of Quantum Chemistry

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“…Depending on the starting compounds, different systems of solvent/catalyst [13] and ratios of reagents [9,14,15] may be used, but heating is needed in all cases.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Acylation of 4-Chloroalkyl-3,4-dihydropyrimidin-2(1H)- ones

Колосов

Кулык

Al‐Ogaili

et al. 2012

Zeitschrift Für Naturforschung B

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4-Chloroalkyl-3,4-dihydropyrimidin-2(1H)-ones are useful multifunctional 3,4-dihydropyrimidine building blocks with low molecular weight and sufficient solubility, which may be modified selectively by substituents in different positions. Here we propose a simple one-pot protocol for the synthesis of these compounds, which is based on the use of common reagents viz. urea, chloroaliphatic aldehydes and 3-ketoesters. Acylation of 4-chloroalkyl-3,4-dihydropyrimidin-2(1H)-ones by carboxylic acid anhydrides leads to 3-acyl derivatives.

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“…A large number of reports are available in literature for this protocol [21][22][23], including a few examples of Biginelli reaction in water [24,25]. A summary of the optimized experiments with benzaldehyde, ethyl acetoacetate and urea is listed in Table 3.…”

Section: Catalytic Activitiesmentioning

confidence: 99%

Assessment of the Catalytic Activities of Novel Brönsted Acidic Ionic Liquid Catalysts

Srivastava

2010

Catal Lett

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Brönsted acidic ionic liquids (BILs) were synthesized by a two step synthetic protocol. Catalytic activities of BILs were assessed by means of suitable catalytic reactions such as acylation of 2-methoxynapthalene with acetic anhydride, Biginelli reaction to synthesize 3,4-dihydropyrimidin-2(1H)-one, stereoselective synthesis of b-amino ketone via direct Mannich-type reaction and esterification of hexanoic acid with benzyl alcohol. Catalytic activities of BILs were high when compared with those of solid acid catalysts such as ZSM-5, beta, dealuminated beta and Al-SBA-15. BILs catalysts were found to be highly stereo/ regio-selective for above mentioned reactions. Novel BILs catalyst offers several attractive features such as low cost, high catalytic activity/selectivity and recyclability.

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Concise Synthesis of Guanidine-Containing Heterocycles Using the Biginelli Reaction

Cited by 92 publications

References 55 publications

Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid

Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid

Synthesis and Acylation of 4-Chloroalkyl-3,4-dihydropyrimidin-2(1H)- ones

Assessment of the Catalytic Activities of Novel Brönsted Acidic Ionic Liquid Catalysts

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