Preparation of Benzylidene Barbituric Acids Promoted by Infrared Irradiation in Absence of Solvent

Alcerreca, Guadalupe; Sanabria, Rubén; Miranda, René; Arroyo, Gonzalo; Tamariz, Joaquı́n; Delgado, Francisco

doi:10.1080/00397910008087151

Cited by 52 publications

(31 citation statements)

References 19 publications

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“…[9][10][11][12] Benzylidenebarbiturates are employed in several well known reactions in the literature 10,[13][14][15][16][17] and have even been used as methionine aminopeptidase inhibitors. 18 The preparation of the 5-chloro-5-benzolbarbiturates was Vol.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and in vivo evaluation of 5-chloro-5-benzobarbiturates as new central nervous system depressants

Vieira¹,

Gomes²,

Matheus³

et al. 2011

J. Braz. Chem. Soc.

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Uma nova família de barbituratos, ácidos 5-cloro-5-benzilbarbitúricos, foi preparada usando um método simples e eficiente a partir de aldeídos aromáticos e ácido barbitúrico, seguido de redução e cloração usando ácido tricloroisocianúrico, com rendimento global de 53 a 70%. Por avaliação in vivo com camundongos, os produtos apresentaram atividade tranqüilizante.A new family of barbiturates, 5-chloro-5-benzylbarbituric acids, was prepared using a simple efficient synthetic method from aromatic aldehydes and barbituric acid, followed by reduction and chlorination with trichloro-isocyanuric acid, affording overall yields of 53 to 70%. The in vivo evaluation with mice showed that these compounds present tranquilizing activity.Keywords: 5-chloro-5-benzylbarbituric acids, tranquilizers, benzylidenebarbiturates, trichloroisocyanuric acid, rota-rod tests IntroductionBarbiturates are very well known drugs with activity at the central nervous system (CNS), with specific activity as anticonvulsants, anxiolytics, tranquilizers and sedatives-hypnotics. 1 The mechanism of action of barbiturates at the CNS is not well known, but it has been shown that they are able to interfere with acetylcholine, norepinephrine and glutamate activity and also that they can inhibit the calcium uptake of nerve terminals, thus allowing their use as analgesics. 2,3 In fact, today barbiturates are commonly used to induce anesthesia in surgery procedures. They are also known as GABA-mimetics, thus functioning as agonists of GABA receptors. 3,4 For many years the barbiturates were the main drugs used to cause effects on the CNS. However, after the discovery of the very effective benzodiazepines, their use became less common simply because benzodiazepines have less potential for lethal overdoses. 5,6 The main cause of death by overdoses of barbiturates is respiratory failure, because they are very potent respiratory depressants. Today, the main uses of barbiturates are the induction of anesthesia and for the treatment of refractory status epilepticus. 7 Regarding the significant historical and actual use of barbiturates as neurological drugs, and the importance of this type of disease in the actual condition of mankind, we developed a very simple new family of barbiturates with CNS activity. Interestingly, 5-chlorobarbituric acid and their derivatives have been rarely investigated. The only similar compounds that have been reported as anticonvulsants are the 5-chloro-5-phenyl barbiturates. 8 Surprisingly, 5-benzyl-5-chlorobarbituric acids have not been reported in the literature. We developed a very simple and efficient method for the preparation of this new family of barbiturates as potential tranquilizers. Results and DiscussionOur strategy for the preparation of 5-benzyl-5-chlorobabiturates was based on the use of benzylidenebarbiturates as intermediates, which are very easy to prepare. [9][10][11][12] Benzylidenebarbiturates are employed in several well known reactions in the literature 10,13-17 and have even been used as methionine aminopeptidas...

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Section: Resultsmentioning

confidence: 99%

Synthesis and in vivo evaluation of 5-chloro-5-benzobarbiturates as new central nervous system depressants

Vieira¹,

Gomes²,

Matheus³

et al. 2011

J. Braz. Chem. Soc.

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“…Additionally, some of them have been recently studied as non-linear optical materials and dyes [5]. Various methods have been reported for the Knoevenagel condensation of carbonyl compounds with barbituric acids or 2-thio barbituric acids like homogeneous systems [6][7][8], solvent-free grinding using NH 2 SO 3 H [9], microwave irradiation [10], infra red promoted [11], ionic liquid mediated condensation [12], various acid and base catalyzed condensation reactions including dry condensation with acidic clay catalysts [13][14][15][16][17][18][19][20]. Recently, Ni supported on SiO 2 has been used for the selective catalytic Knoevenagel condensation [21].…”

Section: Introductionmentioning

confidence: 99%

Nickel Nanoparticles Catalyzed Knoevenagel Condensation of Aromatic Aldehydes with Barbituric Acids and 2-Thiobarbituric Acids

Khurana

Vij

2010

Catal Lett

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“…The product has a very low solubility in cold methanol. Separation of the product from traces of both reactants involves a simple filtration of the reaction mixture followed by washing the crystals with May-Jun 2001 655 [a] Isolated yields; [b]All products have identical 1 H and 13 C nmr spectra as authentic samples reported elsewhere [9][10][11][12][13][14][15][16].…”

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confidence: 99%

A simple method for knoevenagel condensation of α,β‐conjugated and aromatic aldehydes with barbituric acid

Jursic

2001

Journal of Heterocyclic Chem

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Preparation of Benzylidene Barbituric Acids Promoted by Infrared Irradiation in Absence of Solvent

Cited by 52 publications

References 19 publications

Synthesis and in vivo evaluation of 5-chloro-5-benzobarbiturates as new central nervous system depressants

Synthesis and in vivo evaluation of 5-chloro-5-benzobarbiturates as new central nervous system depressants

Nickel Nanoparticles Catalyzed Knoevenagel Condensation of Aromatic Aldehydes with Barbituric Acids and 2-Thiobarbituric Acids

A simple method for knoevenagel condensation of α,β‐conjugated and aromatic aldehydes with barbituric acid

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