Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV-vis spectra, and DFT calculations.

Tetrazolium-5-aminides have been prepared by the -butylation of 5-aminotetrazole and its -methyl derivatives by the BuOH/HClO system followed by the treatment of the tetrazolium salts by alkali. The mesoionic compounds have been found to show a higher reactivity of the exocyclic N atom in comparison with 5-aminotetrazoles. The compounds reacted with 1,2-dibromoethane and 5-(methylsulfonyl)-1-phenyl-1-tetrazole with substitution of bromine and methylsulfonyl groups giving the corresponding tetrazolium salts or conjugate aminides.

Mimics of Pincer Ligands: An Accessible Phosphine-Free -(Pyrimidin-2-yl)-1,2-azole-3-carboxamide Framework for Binuclear Pd(II) Complexes and High-Turnover Catalysis in Water.

We report for the first time cyclic phosphine-free "head to tail" N,N,N pincer-like (pincer complexes mimicking) -(pyrimidin-2-yl)-1,2-azole-3-carboxamide Pd(II) complexes with deprotonated amide groups as high-turnover catalysts (TON up to 10, TOF up to 1.2 × 10 h) for cross-coupling reactions on the background of up to quantitative yields under Green Chemistry conditions. The potency of the described catalyst family representatives was demonstrated in Suzuki-Miyaura, Mizoroki-Heck, and Sonogashira reactions on industrially practical examples.

5-(2-Mercaptoethyl)-1H-tetrazole: Facile Synthesis and Application for the Preparation of Water Soluble Nanocrystals and Their Gels.

A facile method for the preparation of the novel capping ligand 5-(2-mercaptoethyl)-1H-tetrazole for the stabilization of water-soluble nanocrystals was developed. This effective synthetic procedure is based on the cycloaddition of sodium azide to 3,3'-dithiobis(propionitrile) followed by the reductive cleavage of a S-S bond with triphenylphosphine. The structure of the synthesized compound was confirmed by single-crystal X-ray analysis.

The first organocopper tetrazole derivative: synthesis and characterization.

1-(5-Amino-3-azapentyl)tetrazole dihydrochloride (HL·2HCl) was prepared by heterocyclization of diethylenetriamine with triethyl orthoformate and sodium azide followed by treatment with potassium carbonate and hydrochloric acid. The reaction of CuCl2, HL·2HCl and triethylamine (NEt3) in a molar ratio of 1 : 1 : 3 in water was found to generate a novel organometallic tetrazole derivative Cu2L2Cl2. This compound is present as a binuclear centrosymmetric molecular complex, in which C-deprotonated tetrazole L acts as a chelating ligand via the two amino N and tetrazole ring C coordination sites and the two copper atoms are linked together through two tetrazole ring N(4)-C(5) bridges.

Copper(II) tetrafluoroborate complexes with the N(3),N(4)-bridging coordination of 1-(tert-butyl)-1H-tetrazole: synthesis, crystal structure and magnetic properties.

1-(tert-Butyl)-1H-tetrazole (L) reacts with copper(ii) tetrafluoroborate hexahydrate to give the complexes [Cu2L8(H2O)2](BF4)4 (1) or [Cu3L6(H2O)6](BF4)6 (2) depending on the reaction conditions. These complexes, as well as compound L, were characterized using single crystal X-ray analysis. Complex 1 was found to comprise a dinuclear complex cation [Cu2L8(H2O)2](4+) (the Ci symmetry point group), with six tetrazole ligands L showing monodentate N(4)-coordination, and two ligands L providing two tetrazole ring N(3),N(4) bridges between the copper(ii) cations; water molecules complete the distorted octahedral coordination of the metal ions.