Unique charge-separated intermolecular and eight-membered intramolecular H-bonds in bis-(thio)barbiturates

Crossed one-pot reaction of mixed cyclic b-dicarbonyl with various aldehydes in the presence of cyanogen bromide and triethylamine leads to the selective and efficient formation of crossed new unsymmetrical spiro dihydrofurans at room temperature. The products were obtained in good to excellent yields. Structure elucidation was carried out by 1 H NMR, 13 C NMR, FT-IR spectroscopy, Mass analyses and X-ray crystallography technique. A proposed mechanism was discussed for the formation of products. ArticleNoroozi Pesyan et al. Scheme 1 One-pot cascade selective reaction of the mixture of an aldehyde (4a-4e) and two different cyclic b-dicarbonyl compounds Scheme 2 One-pot cascade selective reaction of 1 and 2 with 4 (top), 2 and 3 with 4 (bottom) in the presence of BrCN and triethylamine Scheme 3 Mechanism of the formation of 6a as a representative

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Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et₃N

Pesyan

Shokr

Gharib

et al. 2015

J Chinese Chemical Soc

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Synthesis of New Tetrazole Derivatives of Spiro‐ and Bis‐barbiturates

Kashani

Pesyan

Şahin

2015

J Chinese Chemical Soc

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This work described the synthesis of the first and unprecedented examples of 5-aryl-1H-tetrazoles including spiro-and bis-(thio)barbiturates, generated from the reaction between 4-(1H-tetrazol-5-yl)benzaldehyde with (thio)barbituric acids and cyanogen bromide (BrCN) in the presence of triethylamine, providing good overall yields. Tetrazoles based on bis-(thio) barbiturates were also obtained in the absence of BrCN under the same conditions. The structures were characterized by IR, 1 H NMR, 13 C NMR, X-ray crystallography and mass analysis techniques. The reaction mechanism was proposed. The hydrogen bond strength (E HB ) versus d (O1·····O7 (w)) distance (kcal.mol -1 ) and corresponding pKa value for the proton of H 3A (in water molecule) in 4b.H 2 O were estimated to be 13.8 kcal.mol -1 and 8.2, respectively.

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4‐Methyl morpholinium bis‐(thio)barbiturates: Synthesis, structure, anticancer evaluation, and CoMFA study

Pesyan

Rashidnejad

Esmaeili

et al. 2020

J Chinese Chemical Soc

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The reaction of symmetrical (thio)barbituric acids with aldehydes in the presence of 4-methyl morpholine yielded a new form of 4-methyl morpholinium bis-(thio)barbiturate containing charge-separated intermolecular and eightmembered intramolecular H-bonds. X-ray Crystallography, FT-IR, and 1 H and 13 C-NMR spectroscopy techniques were used for structure characterizations. Some of these compounds showed potent anticancer activities. Cytotoxicity of the synthetic compounds against HeLa and MCF-7 cell lines were performed by MTT assay. In addition, a comparative molecular field analysis was carried out, and the effects of substituents on the biological activities of these compounds were explained.

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Unique charge-separated intermolecular and eight-membered intramolecular H-bonds in bis-(thio)barbiturates

Cited by 6 publications

References 40 publications

Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et₃N

Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et₃N

Synthesis of New Tetrazole Derivatives of Spiro‐ and Bis‐barbiturates

4‐Methyl morpholinium bis‐(thio)barbiturates: Synthesis, structure, anticancer evaluation, and CoMFA study

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Unique charge-separated intermolecular and eight-membered intramolecular H-bonds in bis-(thio)barbiturates

Cited by 6 publications

References 40 publications

Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et3N

Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et3N

Synthesis of New Tetrazole Derivatives of Spiro‐ and Bis‐barbiturates

4‐Methyl morpholinium bis‐(thio)barbiturates: Synthesis, structure, anticancer evaluation, and CoMFA study

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Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et₃N

Regioselective One‐pot Synthesis of New Unsymmetric Spiro Dihydrofurans in the Reaction of Mixed Two Different Cyclic β‐Dicarbonyl Compounds with BrCN and Aldehydes in the Presence of Et₃N