Practical synthesis of 1,4-dioxane derivative of the closo-dodecaborate anion and its ring opening with acetylenic alkoxides

Sivaev, Igor B.; Kulikova, Nadezhda Yu.; Nizhnik, Evgeniya A.; Vichuzhanin, M. V.; Starikova, Z. A.; Semioshkin, Andrey; Bregadze, V. I.

doi:10.1016/j.jorganchem.2007.11.027

Cited by 62 publications

(42 citation statements)

References 37 publications

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“…Dioxonium derivative 1 was synthesized according to the proce dure, which we have developed earlier. 11 Tetrabutylammonium {2 [2 (4 formylphenoxy)ethoxy]etho xy}undecahydro closo dodecaborate (2). A mixture of com pound 1 (0.5 g, 1.06 mmol), 4 hydroxybenzaldehyde (0.125 g, 1.06 mmol), Bu 4 NBr (0.34 g, 1.06 mmol), and K 2 CO 3 (2 g) was refluxed in MeCN (10 mL) for 10 h. Then excess potassium carbonate was filtered off, acetonitrile was evaporated, and prod uct 2 was precipitated by adding water (5 mL 11 (1) …”

Section: Methodsmentioning

confidence: 99%

Synthesis of new building blocks based on the closo-dodecaborate anion

et al. 2008

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The reactions of the dioxonium derivative of closo dodecaborate(12) with aromatic alde hydes and esters containing O and N nucleophilic centers were studied. These reactions were used to synthesize new closo dodecaborate based building blocks containing aldehyde and acid ic groups.Among a broad range of boron compounds, functional derivatives of the closo dodecaborate dianion [B 12 H 12 ] 2-are the most interesting as promising agents for boron neu tron capture therapy (BNCT) of cancer. 1 This is associat ed with their low toxicity, as well as with high solubility of their alkali metal salts in water. The sodium salt of mer capto closo dodecaborate Na 2 [B 12 H 11 SH] is one of two drugs for BNCT used in clinical practice. 2 The main prob lem in the chemistry of [B 12 H 12 ] 2-is that the cluster con tains 12 equivalent boron vertices, which strongly hinders the introduction of a reaction center. The synthesis of cy clic oxonium derivatives of [B 12 H 12 ] 2-(1) and their cleav age by nucleophiles was a breakthrough in the chemistry of this dianion. 3-5 This approach was used to synthesize de rivatives of the B 12 cluster with various active molecules, such as natural porphyrins, 6 phthalocyanines, 7 cholester ols, 8 coumarins, 9 etc. Oxonium derivatives can also be used in the synthesis of building blocks, i.e., derivatives con Scheme 1

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Section: Methodsmentioning

confidence: 99%

Synthesis of new building blocks based on the closo-dodecaborate anion

et al. 2008

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“…[11][12][13] The second approach is based on the preparation of cyclic oxonium derivatives of closo-dodecaborate followed by ring opening with various nucleophilic reagents. [14] This method is very efficient for the synthesis of derivatives with pendant functional groups connected to the boron cage through flexible spacers of 5-6 atoms and can be successfully applied to other types of polyhedral boron hydrides. [15] The decahydro-closo-decaborate anion, [B 10 H 10 ] 2-, is another member of the [B n H n ] 2-family.…”

Section: Main Types Of Polyhedral Boron Hydridesmentioning

confidence: 99%

Polyhedral Boranes for Medical Applications: Current Status and Perspectives

2009

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“…Acetonitrile was distilled from P 2 O 5 and then from CaH 2 . Oxonium derivative 1, and ethyl 4-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]piperazine-1-carboxylate were prepared according to the described methods [15,16]. The 1 H, 13 C and 11 B NMR spectra were recorded at 400.13, 100.61 and 128.38 MHz, respectively, on a BRUKER-Avance-400 spectrometer.…”

Section: Materials and Equipmentmentioning

confidence: 99%