Polynuclear Branched Tetrazole Systems. 2. New 2-(5-Tetrazolyl)ethylpodands and Their NH-Acidity

Zubarev, V. Yu.; Bezklubnaya, E. V.; Pyartman, A. K.; Trifonov, R. E.; Островский, В. А.

doi:10.1023/b:cohc.0000010646.77507.bb

Cited by 8 publications

(6 citation statements)

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“…Salts 12 are often prepared using more readily available 5-aminotetrazole (13) instead of tetrazole 10. Upon nitration with polynitro compounds in the presence of an alkali, compound 13 is converted into 5-nitraminotetrazolate(27) salts (12) (yields 68% ± 91%). 30 M = Li, Na, K, Rb, Cs.…”

Section: Synthesis Of Metal Derivatives From Tetrazolesmentioning

confidence: 99%

Metal derivatives of tetrazoles

Гапоник¹,

2006

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Published data on the synthesis, structure, properties Published data on the synthesis, structure, properties and applications of metal derivatives of tetrazoles are generalised and applications of metal derivatives of tetrazoles are generalised and described systematically. Compounds based on the anionic and described systematically. Compounds based on the anionic and neutral tetrazole forms, and neutral tetrazole forms, C C-and -and N N-mono-and -mono-and C C, ,N N-disubsti--disubstituted tetrazoles are considered. The bibliography includes 464 tuted tetrazoles are considered. The bibliography includes 464 references references. . ReceivedDepending on the reaction conditions, meta-and para-5,5 Hphenyleneditetrazoles 25 react with Cd, Zn and Mn(II) salts to give essentially different, as regards both composition and structure, complexes 26, 27, 44 28, 45 29. 46 The structures of compounds 26 ± 29 were determined by X-ray diffraction. Compounds 26 ± 28 in which the doubly charged anions derived from tetrazole 25 function as bridges are two-and three-dimensional coordination polymers. Conversely, compound 29 is a mononuclear aqua complex containing no metal ± tetrazole coordination bond. In the structure of complex 28, one-dimensional channels were found which occupy up to 35% of the void volume and encapsulate tetrameric cyclic water clusters and DMF molecules. On heating to 150 8C, water and DMF are removed from the channels, which accounts for the interest of researchers in this type of compound for the preparation of inclusion compounds and sorbents. A coordination polymer with a composition similar to complex K + 7

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Section: Synthesis Of Metal Derivatives From Tetrazolesmentioning

confidence: 99%

Metal derivatives of tetrazoles

Гапоник¹,

2006

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“…Examples are 1,3-dipolar cycloaddition of hydrazoic acid salts to polynitriles [6][7][8] and reaction of 1-aryl-5-methylsulfonyltetrazoles with polyfunctional O-nucleophiles [9][10][11]. The latter procedure was applied in the present work.…”

Section: Methodsmentioning

confidence: 99%

Tetrazoles: XLVII. A route to tetrazole-containing dendrimers

2004

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The reaction of 5-methylsulfonyl-1-phenyltetrazole with pentaerythritol in acetonitrile in the presence of sodium hydroxide gave tetrakis(1-phenyltetrazol-5-yloxymethyl)methane. Sulfur-containing analog of the latter was obtained by alkylation of 1-phenyl-4,5-dihydrotetrazole-5-thione with 1,3-dibromo-2,2-bis-(bromomethyl)propane. Nitration of the resulting polytetrazoles afforded the corresponding tetrakis(p-nitrophenyl) derivatives which can be used in the synthesis of tetrazole-containing dendrimers according to the divergent scheme. * For communication XLVI, see [1]. Scheme 1.

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“…[9,10] Coordination chemists have used this strategy to create tetrazoles in their multidentate ligands in the last step of the synthesis (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“…Examples of tetrazole syntheses from nitriles. [9][10][11] Scheme 2. Regioisomers formed when protecting free tetrazoles.…”

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A Synthon for the Convenient and Efficient Introduction of Tetrazolylmethyl Groups into Nucleophile‐Bearing Compounds

et al. 2010

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International audienceAn activated synthon for the efficient introduction of a protected tetrazolylmethyl group into nucleophile-bearing compounds is presented. The β-cyanoethyl protecting group allows for very effective deprotection under mild basic conditions. The synthon can be prepared by a two-step procedure (42 %) starting from cheap starting material and can alkylate piperidine in 91 % yield. Even quadruple alkylation to form a protected version of the hexadentate ligand EDTT gives decent yields. Simultaneous removal of the four protecting groups furnishes the lithium salt of a formally zwitterionic ligand in 75 % yield. Finally, the synthon's performance has been assessed by comparison with its benzyl-protected counterpart and was found to be equally efficient in the alkylation of simple amines but superior in deprotection. For substrates bearing basic amine sites, the β-cyanoethyl group is largely preferable

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Polynuclear Branched Tetrazole Systems. 2. New 2-(5-Tetrazolyl)ethylpodands and Their NH-Acidity

Cited by 8 publications

References 1 publication

Metal derivatives of tetrazoles

Metal derivatives of tetrazoles

Tetrazoles: XLVII. A route to tetrazole-containing dendrimers

A Synthon for the Convenient and Efficient Introduction of Tetrazolylmethyl Groups into Nucleophile‐Bearing Compounds

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