Synthesis and biological evaluation of some new spiro derivatives of barbituric acid

Kesharwani, Shailee; Sahu, Nitendra K.; Kohli, D. V.

doi:10.1007/s11094-009-0298-8

Cited by 22 publications

(18 citation statements)

References 5 publications

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“…Substituted pyrazole and barbiturate moieties constitute an important class of compounds in the field of agricultural and medicinal chemistry because of their broad spectrum biological activities (13) . Since, the combination of two or more heterocyclic and nonheterocyclic (14) systems enhances the biological profile more fold than their parent nuclei , so we considered to synthesize ; the pyridazinone has pyrazolyl and / or barbituryl groups in position 4 . Treatment of the acids 1 e , f with N 2 H 4 in boiling ethanol, afforded 6-(p-acetamido phenyl)-4 (3,5-dimethyl pyrazolyl) and / or 2,4dihydroxy pyrimidinyl 6-one) 2,3,4,5 tetrahydro 3(2H) pyridazinone (2 d,e ) .…”

Section: T Results and Discussionmentioning

confidence: 99%

Utility of p-Acetamidobenzoyl Prop-2-enoic Acid in the Synthesis of New α-Amino Acids and Using Them as Building Blocks in Heterocyclic Synthesis

2011

Egypt. J. Chem.

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HE PRESENT work deals with the generation and synthesis of different unnatural amino acid derivatives via treatment of 3-(4acetamidobenzoyl)-prop-2-enoic acid with 5-aryl-2-amino 1, 3, 4 thiadiazole, 3, 5-dimethyl pyrazole and barbituric acid to afford the product of conjugate addition acids (1) respectively. Additionally, the adduct 1 are used as key starting materials to synthesize some heterocycles include pyridazene , furanone and oxazine derivatives. The antimicrobial screening of some of the synthesized compounds was done using the agar diffusion assay

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Section: T Results and Discussionmentioning

confidence: 99%

Utility of p-Acetamidobenzoyl Prop-2-enoic Acid in the Synthesis of New α-Amino Acids and Using Them as Building Blocks in Heterocyclic Synthesis

2011

Egypt. J. Chem.

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“…Beside the biological importance, these spirocycles have been extensively used for the synthesis of novel ligands, catalysts and some special organic optoelectronics synthetic materials (Saragi et al, 2007;Xie and Zhou, 2008;Ding et al, 2009). In addition, recent literature review suggests that the diazaspiro [5.5]undecane-1,3,5,9-tetraones motif has a wide range of therapeutic and biological properties such as CNS depressant , anticonvulsant (Rajopadhye and Popp, 1988), potent sedative-hypnotic (Kesharwani et al, 2009), antibacterial (Goel et al, 2005) and fungicidal (Behera et al, 2009). Moreover, these types of compounds can also be used as a yellow organic pigment and as a disperse dye with strong fluorescence property as it contains barbituric acid moiety (Theford et al, 2003;Karci, 2008;Wang and Kim, 2009).…”

Section: Introductionmentioning

confidence: 99%

Stereoselective synthesis of diazaspiro[5.5]undecane derivatives via base promoted [5+1] double Michael addition of N,N-dimethylbarbituric acid to diaryliedene acetones

Islam

Barakat

Al‐Majid

et al. 2017

Arabian Journal of Chemistry

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The nitrogen containing spiro-heterocycle is one of the privileged synthetic motif that constitutes various naturally occurring molecules and displays a broad range of pharmaceutical and biological activities. A new methodology was developed for the synthesis of 2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraones spiro-heterocyclic derivatives via cascade cyclization of [5+1] double Michael addition reaction of N,N-dimethylbarbituric acid with the derivatives of diaryldivinylketones in the presence of diethylamine at ambient temperature. The developed protocol is highly capable of furnishing diazaspiro[5.5]undecane derivatives 3a-m in excellent yields (up to 98%), from easily accessible symmetric and non-symmetric divinylketones 2a-m, containing aryl and heteroaryl substituents. The diazaspiro-heterocyclic structure was mainly elucidated by NMR and X-ray crystallographic techniques. The single-crystal X-ray studies revealed that, the

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“…Spiro compounds have been reported to possess biological activities that include anti-inflammatory activity [34], anticonvulsant, CNS depressant [35], narcotic [36], hypotensive, analgesic [37]. Several works have been reported for the synthesis of other spiro barbiturates [38][39][40][41][42][43][44].…”

Section: Introductionmentioning

confidence: 99%

“…As we searched in the literature, there are some reports about spiro barbiturates based on bis-arylideneacetones [36,45] and no report about spiro barbiturates based on 2,6-bisarylidenecyclohexanones. Based on these concepts, in this research, we report a new and facile route for the synthesis of 5,5-two substituted spiro-barbiturates by the condensation reaction of N-substituted and unsubstituted (thio)barbituric acids with dibenzalacetone and 2,6-dibenzylidenecyclohexanone derivatives.…”

Section: Introductionmentioning

confidence: 99%

New spiro (thio) barbiturates based on cyclohexanone and bicyclo [3.1.1]heptan-6-one by nonconcerted [1+5] cycloaddition reaction and their conformational structures

Pesyan¹,

Noori²,

Poorhassan³

et al. 2014

Bull. Chem. Soc. Eth.

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ABSTRACT. Crossed-aldol condensation reaction of aromatic aldehydes with ketones such as; acetone and cyclohexanone leads to the efficient formation of cross conjugated α,β-unsaturated ketones in excellent yield. The intermolecular and then intramolecular Michael addition reaction of α,β-unsaturated ketones derived from acetone and cyclohexanone with (thio)barbituric acids lead to synthesis new type of 7,11-diaryl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone and 2,4-diaryl-1'H-spiro[bicyclo[3.3.1]nonane-3,5'-pyrimidine]-2',4',6',9(3'H)-tetraone, respectively in good yield. Structure elucidation is carried out by 1 H NMR, 13C NMR, FT-IR, UV-Visible, mass spectroscopy and X-ray crystallography techniques. A possible mechanism of the formation is discussed. The structural conformation also demonstrated by coupling constants derived from dihedral angles between vicinal and geminal protons. The 1 H NMR spectra of NH protons of spiro compounds derived from barbituric acid show a broad singlet peak instead, these protons in the spiro compounds derived from thiobarbituric acid show two distinct peaks.

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Synthesis and biological evaluation of some new spiro derivatives of barbituric acid

Cited by 22 publications

References 5 publications

Utility of p-Acetamidobenzoyl Prop-2-enoic Acid in the Synthesis of New α-Amino Acids and Using Them as Building Blocks in Heterocyclic Synthesis

Utility of p-Acetamidobenzoyl Prop-2-enoic Acid in the Synthesis of New α-Amino Acids and Using Them as Building Blocks in Heterocyclic Synthesis

Stereoselective synthesis of diazaspiro[5.5]undecane derivatives via base promoted [5+1] double Michael addition of N,N-dimethylbarbituric acid to diaryliedene acetones

New spiro (thio) barbiturates based on cyclohexanone and bicyclo [3.1.1]heptan-6-one by nonconcerted [1+5] cycloaddition reaction and their conformational structures

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