Salts of 5-Substituted Uracils with 1,8-Diazabicyclo[5.4.0]-undec-7-ene: Convenient Reagents for Nucleophilic Addition and Substitution Reactions

Suwiński, J.; Walczak, Krzysztof

doi:10.1055/s-2001-10805

Cited by 9 publications

(5 citation statements)

References 24 publications

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“…DBU and 3,3,6,9,9-pentamethyl-2,10-diazabicyclo[4.4.0]dec-1-ene (PMDBD) 10 in acid−base reactions, with the formation of adducts involving the corresponding amidinium cation, are examples of the behavior of amidines as bases, as expected according to their p K a (conjugate acid p K ) values, which are greater than 23 …”

Section: Introductionmentioning

confidence: 76%

Activation of Carbon Dioxide by Bicyclic Amidines

et al. 2004

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Activation of the carbon dioxide molecule was achieved using bicyclic amidines (DBU, PMDBD, and DBN). The solution reaction of CO(2) with amidines yielded the corresponding zwitterionic complexes through the formation of a N-CO(2) bond. (13)C NMR data confirmed the carbamic nature of the carbamic zwitterions, DBU-CO(2) and PMDBD-CO(2). However, when these adducts were crystallized, the X-ray analyses of the single crystals were in agreement with bisamidinium bicarbonate salt structures, indicating that structural changes occurred in the crystallization process. The elemental and thermogravimetric analysis data for the carbamic zwitterions, DBU-CO(2) and PMDBD-CO(2), initially obtained by the direct reaction of amidines with CO(2), suggest that these molecules are probably associated with one molecule of water by hydrogen-bond formation (amidinium(+)-COO(-)...H(2)O). A correlation was observed between the thermal stability and the transcarboxylating activity for the amidine-CO(2) complexes. Theoretical calculations of hardness were performed at the B3LYP/cc-pVTZ level of theory and showed concordance with the experimental reactivity of DBU and PMDBD toward CO(2).

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Section: Introductionmentioning

confidence: 76%

Activation of Carbon Dioxide by Bicyclic Amidines

et al. 2004

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“…[17] In contrast, triethylammonium salts 2 do not react with alkyl halides or tosylates in boiling acetonitrile. Potassium salts, which can easily be prepared Scheme 3.…”

Section: Resultsmentioning

confidence: 99%

Treatment of Polyfluoro-1,1-dihydroalkyl Sulfones with Sodium Cyanate and Triethylamine: A New Method for the Synthesis of 6-(Polyfluoroalkyl)uracils

et al. 2002

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“…Since we also wanted to investigate the biological effect of the free amidinium salts, we attempted their direct production based on literature examples [ 23 , 35 ], by rapid synthesis without the use of protecting groups ( Scheme 3 ). For this rapid synthetic method, we first synthesized the 6- O -tosyl derivative of methyl α- d -glucopyranoside ( 40 ) [ 36 , 37 ], then reacted this compound with DBU in dry acetonitrile. Neither the expected DBU-conjugated derivative nor the 5,6-eliminated derivative was formed in the reaction.…”

Section: Resultsmentioning

confidence: 99%

“…Reaction 1 : To the solution of compound 40 [ 36 , 37 ] (500 mg, 1.436 mmol) in dry CH 3 CN (8.5 mL), DBU (1288 μL, 8.618 mmol, 6.0 equiv.) was added.…”

Section: Methodsmentioning

confidence: 99%

First Synthesis of DBU-Conjugated Cationic Carbohydrate Derivatives and Investigation of Their Antibacterial and Antifungal Activity

Demeter

Török

Kiss

et al. 2023

IJMS

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The emergence of drug-resistant bacteria and fungi represents a serious health problem worldwide. It has long been known that cationic compounds can inhibit the growth of bacteria and fungi by disrupting the cell membrane. The advantage of using such cationic compounds is that the microorganisms would not become resistant to cationic agents, since this type of adaptation would mean significantly altering the structure of their cell walls. We designed novel, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)-derived amidinium salts of carbohydrates, which may be suitable for disturbing the cell walls of bacteria and fungi due to their quaternary ammonium moiety. A series of saccharide-DBU conjugates were prepared from 6-iodo derivatives of d-glucose, d-mannose, d-altrose and d-allose by nucleophilic substitution reactions. We optimized the synthesis of a d-glucose derivative, and studied the protecting group free synthesis of the glucose-DBU conjugates. The effect of the obtained quaternary amidinium salts against Escherichia coli and Staphylococcus aureus bacterial strains and Candida albicans yeast was investigated, and the impact of the used protecting groups and the sugar configuration on the antimicrobial activity was analyzed. Some of the novel sugar quaternary ammonium compounds with lipophilic aromatic groups (benzyl and 2-napthylmethyl) showed particularly good antifungal and antibacterial activity.

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Salts of 5-Substituted Uracils with 1,8-Diazabicyclo[5.4.0]-undec-7-ene: Convenient Reagents for Nucleophilic Addition and Substitution Reactions

Cited by 9 publications

References 24 publications

Activation of Carbon Dioxide by Bicyclic Amidines

Activation of Carbon Dioxide by Bicyclic Amidines

Treatment of Polyfluoro-1,1-dihydroalkyl Sulfones with Sodium Cyanate and Triethylamine: A New Method for the Synthesis of 6-(Polyfluoroalkyl)uracils

First Synthesis of DBU-Conjugated Cationic Carbohydrate Derivatives and Investigation of Their Antibacterial and Antifungal Activity

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