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2 Polish Journal of Chemistry

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Regioselective Synthesis of New Chelating Bistetrazole Ligands and Study of Their Coper(II) Complexes

Voitekhovich S., Gaponik P. N., Pytleva D. S., Lyakhov A. S., Ivashkevich O. A.

Polish Journal of Chemistry

2002

Vol. 76 / nr 10

1371-1380

Synthesis of some new N-substituted bistetrazoles is described. 1,5-Bis(2-tert-butyl- 5-tetrazolyl)-3-oxopentane (btop) is obtained by regioselective alkylation of 1,5-bis(5- tetrazolyl)-3-oxopentane with tert-butyl alcohol in 96% sulphuric acid media. 1,5-Bis(1- methyl-5-tetrazolyl)-3-oxopentane (mtop) is synthesized by exhaustive methylation of 1,5-bis(2-tert-butyl-5-tetrazolyl)-3-oxopentane followed by the removal of tert-butyl group from the formed tetrazolium methyl sulphate in acidic conditions. Isomeric tetrazolium perchlorate is converted in analogous conditions to perchlorate of 1,5-bis(1- methyl-5-tetrazolyl)-3-oxopentane. Synthesized bistetrazoles are found to react with copper(II) chloride in ethyl alcohol or acetone solutions giving solid [Cu(mtop)Cl2] and [Cu(btop)Cl2] complexes. Perchlorate of 1,5-bis(1-methyl-5-tetrazolyl)-3-oxopentane reacts with copper(II) chloride in ethyl alcohol leading to formation of complex [Cu(mtop)Cl2], whereas in aqueous solution complex [Cu(mtop)2](ClO4)2 is formed. According to X-ray study of chloride complexes, Cu(II) is surrounded by a tridentate chelating ligand and two halide anions resulting in distorted square pyramidal geometry.

Synthesis and Transformation of 1-Monosubstituted Tetrazoles to Pyrimidinones, Benzoxazoles and Quinazolinediones Through 1,4-Disubstituted Tetrazolium Salts

Voitekhovich S., Gaponik P. N., Lyakhov A. S., Ivashkevich O. A.

Polish Journal of Chemistry

2001

Vol. 75, nr 2

253-264

Synthesis and some new transformations of 1-aryltetrazoles into other heterocycles through 1,4-disubstituted tetrazolium salts are described. 1-Aryltetrazoles, quaternized with tert-butanol and diacetone alcohol in perchloric acid media, gave pure 1,3- or 1,4-disubstituted tetrazolium salts or their mixtures. 1,3-Disubstituted tetrazolium salts are slowly converted into the corresponding 1,4-salts under dissolving in perchloric acid. 1,4-Disubstituted tetrazolium salts are recyclized to 2-alkylaminobenzoxazoles, 3-monosubstituted 2,4-quinazolinediones and mixtures of di- and tetrahydropyrimidin-2(1H)- ones in basic conditions.