Über 1.2.4‐Triazole, XVII. Die Nitrierung und Bromierung von 1.2.4‐Triazolonen

Kröger, Carl‐Friedrich; Miethchen, Ralf; Frank, H. P.; Siemerl, Manfred; Pilz, Susanne

doi:10.1002/cber.19691020307

Cited by 28 publications

(8 citation statements)

References 9 publications

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“…NTO displays acidic properties. Its pK a value equals to 3.76 [15,19]. The NTO pK a value shows that this compound is more acidic than acetic acid (pK a = 4.67) and less acidic than chloroacetic acid (pK a = 2.86).…”

Section: Introductionmentioning

confidence: 97%

Computational study of NTO (5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one) tautomeric properties in aqueous solution

Golius

Gorb²,

Scott

et al. 2015

Struct Chem

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This study focuses on elucidating the stable forms of a new energetic material that is a member of the class of insensitive munitions (IM), 5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one (NTO), including its tautomers, and anions. The geometry and properties of all compounds were calculated using density functional theory (M06-2X) and MP2 quantum chemical approaches. Calculations were carried out in the gas phase and in aqueous solution. Chemical stability of these compounds was evaluated in terms of the Gibbs free energy change. Two different solvation models were applied (CPCM and PCM). Calculations showed that overall differences in the results obtained using these two solvation models are negligible for all compounds considered. All possible NTO tautomers were examined and the results are in good agreement with previous studies performed in the gas phase. The stability order was revealed to be slightly dependent on the method applied. In order to estimate acidic properties of NTO, anions of several NTO tautomers were analyzed. In addition, pK a values were calculated using different approaches. As compared with available experimental data it was found that the conductor-like screening model for real solvents approach leads to more accurate estimation of the pK a value than the CPCM and PCM approaches. The pK a value calculated using PCM and CPCM data showed large errors; however, it was proven that the pattern of deprotonation energy was correctly estimated.

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Section: Introductionmentioning

confidence: 97%

Computational study of NTO (5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one) tautomeric properties in aqueous solution

Golius

Gorb²,

Scott

et al. 2015

Struct Chem

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“…In order to obtain an oxo substituent in the 5 position of the 1,2,4-triazole nucleoside (26), displacement of the 5-bromo group of 21 with concomitant deacetylation was effected with sodium benzyloxide in benzyl alcohol at room temperature. After column chromatography of the crude reaction mixture to remove benzyl acetate and excess benzyl alcohol, a 40% yield of 5-benzyloxy-3-nitro-l-(/3-D-ribofuranosyl)-l,2,4-triazole (25) was obtained.…”

mentioning

confidence: 99%

“…After column chromatography of the crude reaction mixture to remove benzyl acetate and excess benzyl alcohol, a 40% yield of 5-benzyloxy-3-nitro-l-(/3-D-ribofuranosyl)-l,2,4-triazole (25) was obtained. Catalytic reduction of the nitro group and simultaneous hydrogenolysis of the benzyl ether with palladium on carbon in the presence of hydrogen afforded the cytidine analog, 3-amino-l-(/3-D-ribofuranosyl)-l,2,4-triazo!in-5-one (26).…”

mentioning

confidence: 99%

Chemical synthesis of the 1,2,4-triazole nucleosides related to uridine, 2'-deoxyuridine, thymidine, and cytidine

Witkowski¹,

Robins²

1970

J. Org. Chem.

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“…reported the nitration of TO with fuming nitric acid/water with yields of NTO up to 67 %. Kroger et al . reported nitration of TO by fuming nitric acid with initial cooling with yields of NTO to 70–75 %.…”

Section: Modified β‐Cyclodextrin Catalyzed Organic Transformationsmentioning

confidence: 99%

β‐Cyclodextrin: A Green and Efficient Supramolecular Catalyst for Organic Transformations

Dalal

Patil

Tayade

2018

The Chemical Record

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β-Cyclodextrin is cyclic oligosaccharide possessing hydrophobic cavity, which binds the substrates selectively and catalyze number of organic transformations with high selectivity. It catalyzes the reaction by non-covalent supramolecular bonding with reversible formation of host-guest complexes as seen in enzymes. This account summarizes our efforts in designing a good number of important organic transformations using β-cyclodextrin and its derivatives. These reactions were performed in neat, aqueous as well as organic media. Greener synthetic routes to a variety of biologically relevant organic molecules has been developed. The temperature, solvent and catalyst amount plays in important role in these reactions. β-Cyclodextrin activates variety of organic compounds like aldehydes, ketones, anhydride, oximes, amines, nitriles and increases the rate of reactions.

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Über 1.2.4‐Triazole, XVII. Die Nitrierung und Bromierung von 1.2.4‐Triazolonen

Cited by 28 publications

References 9 publications

Computational study of NTO (5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one) tautomeric properties in aqueous solution

Computational study of NTO (5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one) tautomeric properties in aqueous solution

Chemical synthesis of the 1,2,4-triazole nucleosides related to uridine, 2'-deoxyuridine, thymidine, and cytidine

β‐Cyclodextrin: A Green and Efficient Supramolecular Catalyst for Organic Transformations

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