Hydrazine in Organic Chemistry

Byrkit, Gordon D.; Michalek, G. A.

doi:10.1021/ie50489a046

Cited by 43 publications

(22 citation statements)

References 89 publications

(120 reference statements)

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“…Synthesis requires excess anhydrous hydrazine and heating, conditions that are not compatible with several functional groups such as carbonyls and alkyl halides, that are susceptible to either nucleophilic addition or reduction. [8] It is therefore difficult to directly introduce 1,2,4,5 - tetrazine onto relatively complex molecules such as fluorophores using this method. Conjugated alkenyl substituted 1,2,4,5-tetrazines were not obtainable from the corresponding alkenyl-nitriles.…”

mentioning

confidence: 99%

In Situ Synthesis of Alkenyl Tetrazines for Highly Fluorogenic Bioorthogonal Live‐Cell Imaging Probes

et al. 2014

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In spite of the wide application potential of 1,2,4,5-tetrazines, particularly in live-cell and in-vivo imaging, a major limitation has been the lack of practical synthetic methods. Here we report the in situ synthesis of (E)-3-substituted-6-alkenyl-1,2,4,5-tetrazine derivatives via an elimination-Heck cascade reaction. Using this strategy, we provide 24 examples of π-conjugated tetrazine derivatives that can be conveniently prepared from tetrazine building blocks and related halides. These include tetrazine analogs of biological small molecules, highly conjugated buta-1,3-diene substituted tetrazines, and a diverse array of fluorescent probes suitable for live-cell imaging. These highly conjugated probes show dramatic fluorescent turn-on (up to 400-fold) when reacted with dienophiles such as cyclopropenes and trans-cyclooctenes, and we demonstrate their application for live-cell imaging. This work provides an efficient and practical synthetic methodology for tetrazine derivatives and will facilitate the application of conjugated tetrazines, particularly as fluorogenic probes for live-cell imaging.

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mentioning

confidence: 99%

In Situ Synthesis of Alkenyl Tetrazines for Highly Fluorogenic Bioorthogonal Live‐Cell Imaging Probes

et al. 2014

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“…If excessive amount of formaldehyde is used, it forms azine, which results in the higher values of hydrazine concentration [41,42]. Optimum quantity of formaldehyde is found to be 1 ml of 30-40% HCHO; whereas use of higher concentration of formaldehyde resulted in unacceptable positive bias.…”

Section: Resultsmentioning

confidence: 96%

Sequential determination of free acidity and hydrazine in presence of hydrolysable ions

Ganesh

Khan²,

Ahmed

et al. 2011

Radiochimica Acta

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Free acidity / Hydrazine / EDTA / Formaldehyde / pH 3.0 / Sodium carbonate / Purex process Summary. A simple method for the sequential determination of free acidity and hydrazine in presence of hydrolysable ions is developed and described. In this method, free acid is titrated with standard sodium carbonate solution after the metal ions in solutions are masked with EDTA. Once the end point for the free acid is determined at pH 3.0, an aliquot of formaldehyde is added to liberate the acid equivalent to hydrazine which is then titrated with the same standard sodium carbonate solution using an automatic titration system. The described method is simple, accurate and reproducible. This method is especially applicable to all ranges of nitric acid and heavy metal ion concentration relevant to Purex process used for nuclear fuel reprocessing. The overall recovery of nitric acid is 98.9% with 3% relative standard deviation. The major advantage of the method is that it uses sodium carbonate a primary standard as titrant and generation of corrosive analytical wastes containing oxalate or sulphate is avoided. Valuable metals like uranium and plutonium can easily be recovered from analytical waste before final disposal.

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“…Nevertheless, this technique has limitations. Synthesis requires excess anhydrous hydrazine and heating, conditions that are not compatible with several functional groups such as carbonyls and alkyl halides, that are susceptible to either nucleophilic addition or reduction 8. It is therefore difficult to directly introduce 1,2,4,5 ‐ tetrazine onto relatively complex molecules such as fluorophores using this method.…”

Section: Optimization Of the Reaction Conditions[a]mentioning

confidence: 99%

In Situ Synthesis of Alkenyl Tetrazines for Highly Fluorogenic Bioorthogonal Live‐Cell Imaging Probes

Yang

Šečkutė

et al. 2014

Angewandte Chemie

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In spite of the wide application potential of 1,2,4,5tetrazines, particularly in live-cell and in vivo imaging, a major limitation has been the lack of practical synthetic methods. Here we report the in situ synthesis of (E)-3-substituted 6alkenyl-1,2,4,5-tetrazine derivatives through an elimination-Heck cascade reaction. By using this strategy, we provide 24 examples of p-conjugated tetrazine derivatives that can be conveniently prepared from tetrazine building blocks and related halides. These include tetrazine analogs of biological small molecules, highly conjugated buta-1,3-diene-substituted tetrazines, and a diverse array of fluorescent probes suitable for live-cell imaging. These highly conjugated probes show very strong fluorescence turn-on (up to 400-fold) when reacted with dienophiles such as cyclopropenes and trans-cyclooctenes, and we demonstrate their application for live-cell imaging. This work provides an efficient and practical synthetic methodology for tetrazine derivatives and will facilitate the application of conjugated tetrazines, particularly as fluorogenic probes for live-cell imaging.

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Hydrazine in Organic Chemistry

Cited by 43 publications

References 89 publications

In Situ Synthesis of Alkenyl Tetrazines for Highly Fluorogenic Bioorthogonal Live‐Cell Imaging Probes

In Situ Synthesis of Alkenyl Tetrazines for Highly Fluorogenic Bioorthogonal Live‐Cell Imaging Probes

Sequential determination of free acidity and hydrazine in presence of hydrolysable ions

In Situ Synthesis of Alkenyl Tetrazines for Highly Fluorogenic Bioorthogonal Live‐Cell Imaging Probes

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