Synthesis and cardiac effects of 3,4-dihydropyrimidin-2(1H)-one-5 carboxylates

Sujatha, K.; Shanmugam, Pachaiyappan; Perumal, Paramasivan T.; Muralidharan, D.; Rajendran, Melani

doi:10.1016/j.bmcl.2006.06.059

Cited by 49 publications

(13 citation statements)

References 12 publications

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“…Within a domestic microwave oven, the synthesis of a number of 4-aryl-3,4-dihydropyrimidinones ( Scheme 3 ) has been reported [ 5 ] illustrating that both Lewis (see above) and Bronsted acids can be effective catalysts in the Biginelli DHPM reaction.…”

Section: The Biginelli Reactionmentioning

confidence: 99%

Microwave Multicomponent Synthesis

Hügel

2009

Molecules

117

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In the manner that very important research is often performed by multidisciplinary research teams, the applications of multicomponent reactions involving the combination of multiple starting materials with different functional groups leading to the higher efficiency and environmentally friendly construction of multifunctional/complex target molecules is growing in importance. This review will explore the advances and advantages in microwave multicomponent synthesis (MMS) that have been achieved over the last five years.

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Section: The Biginelli Reactionmentioning

confidence: 99%

Microwave Multicomponent Synthesis

Hügel

2009

Molecules

117

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“…Recently, Biginelli reactions 6 have attracted much interest in the synthesis of 3,4-dihydropyrimidin-2-(1H)-one/thione derivatives because of their special pharmaceutical and biological activities. For example, these compounds have found use as calcium channel blockers, α-1a-antagonists, 7 and also as antihypertensive, 8 anticancer, 9 anti-HIV, 10 antibacterial, antifungal, 23 or p-dodecylbenzenesulfonic acid. 24 Some of the limitations of these methodologies include low yields, the use of toxic organic solvents and catalysts, harsh reaction conditions and expensive materials.…”

Section: Introductionmentioning

confidence: 99%

Chromium (III) Nitrate Nonahydrate: An Environmentally Benign and Efficient Heterogeneous Catalyst for Facile One-Pot Biginelli Synthesis of 3,4-Dihydropyrimidin-2-(1H)-One/Thione Derivatives Under Solvent-Free Conditions

2016

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Abstract:The use of chromium(III) nitrate nonahydrate (Cr(NO 3 ) 3 ·9H 2 O) as an efficient, mild and economical catalyst for the one-pot three-component Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-one/thione derivatives in the reaction between β-keto esters (methyl or ethyl acetoacetate), aromatic aldehydes (benzaldehye derivatives) and urea or thiourea under thermal and solvent-free conditions with good yields and short reaction times is reported. The most benefits of this synthetic method include the use of an efficient, eco-friendly, inexpensive and non-toxic catalyst, as well as the solvent-free conditions. All products were characterized by 1 H NMR spectroscopy and melting point determination.

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“…In recent years, 3,4‐dihydropyrimidin‐2‐(1 H )‐ones (DHPMs) and thiones have attracted significant attention because of their wide range of biological activities such as antihypertensives (calcium channel modulators), neuropeptide Y antagonists, antifungal, antibacterial, antiviral, anticancer leads (mitotic kinesin Eg5 motor protein inhibitors and blood platelet aggregation inhibitors), antioxidative, anti‐inflammatory, antistaphylococcal antibiotics, and their treating benign prostatic hyperplasia (α‐1a‐adrenergic receptor antagonists) [1–28]. In addition, several isolated marine alkaloids containing the 3,4‐dihydropyrimidinone‐5‐carboxylate skeleton display interesting biological properties [29, 30].…”

Section: Introductionmentioning

confidence: 99%

Magnesium Bromide and Magnesium Chloride Hexahydrate Catalyzed One‐Pot Synthesis of Dihydropyrimidines viaBiginelli Reaction under Solvent‐Free Conditions

Gülten

2013

Journal of Heterocyclic Chem

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Biologically important 12 new important 3,4‐dihydropyrimidin‐2‐(1H)‐ones (‐thiones) were synthesized with in one‐pot three‐component Biginelli reaction from the corresponding aromatic aldehydes (5‐methyl‐2‐thiophenecarboxaldehyde and 2‐chloro‐5‐nitrobenzaldehyde), β‐keto esters (ethylacetoacetate, allylacetoacetate, and t‐butylacetoacetate), and urea/thiourea in the presence of catalytic amount of magnesium bromide and magnesium chloride hexahydrate as nontoxic, inexpensive, and easily available catalysts under solvent‐free conditions at 80 and 100°C. Compared with the catalyst‐free three‐component Biginelli reaction conditions, this method consistently has the advantage of short reaction time (45–100 min) and good to excellent yields (75–91%).

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Synthesis and cardiac effects of 3,4-dihydropyrimidin-2(1H)-one-5 carboxylates

Cited by 49 publications

References 12 publications

Microwave Multicomponent Synthesis

Microwave Multicomponent Synthesis

Chromium (III) Nitrate Nonahydrate: An Environmentally Benign and Efficient Heterogeneous Catalyst for Facile One-Pot Biginelli Synthesis of 3,4-Dihydropyrimidin-2-(1H)-One/Thione Derivatives Under Solvent-Free Conditions

Magnesium Bromide and Magnesium Chloride Hexahydrate Catalyzed One‐Pot Synthesis of Dihydropyrimidines viaBiginelli Reaction under Solvent‐Free Conditions

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