Abstract
A series of 1-benzazolyl-3-methyl(phenyl)-5-[α(β)-naphthyl]formazans was synthesized. A steric effect of the naphthyl group on the structure (tautomerism and state of the intramolecular hydrogen bond) of the azohydrazone grouping was noted. Some tetrazolium salts were obtained by the reaction of the formazans with N-bromosuccinimide. It was established that benzoxazolylformazans are cleaved to 2,5-disubstituted tetrazoles in the process. A method is proposed for the preparation of disubstituted tetrazoles by oxidative cleavage of 1-benzoxazolyl-3,5-diarylformazans.
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N. V. Serebryakova, G. N. Lipunova, N. P. Bednyagina, and L. F. Lipatova, Khim. Geterotsikl. Soedin., 1403 (1970).
N. P. Bednyagina and G. N. Lipunova, Khim. Geterotsikl. Soedin., 877 (1969).
A. P. Zeif, L. N. Shchegoleva, G. N. Lipunova, N. P. Bednyagina, and A. P. Novikova, Zh. Organ. Khim., 6, 1332 (1970).
R. Kuhn and W. Münzing, Ber., 86, 858 (1963).
N. P. Bednyagina and G. N. Lipunova, Khim. Geterotsikl. Soedin., 902 (1968).
Yu. N. Sheinker, I. Ya. Postovskii, N. P. Bednyagina, I. B. Sinyavina, and L. F. Lipatova, Dokl. Akad. Nauk SSSR, 141, No. 6, 1388 (1961).
E. Lieber, D. R. Levering, and I. Patterson, Anal. Chem., 23, 1594 (1951).
E. Wedekind, Ber., 29, 1846 (1896).
Yu. A. Sedov and I. Ya. Postovskii, Zh. Organ. Khim., 5, 781 (1969).
G. N. Lipunova, Master's Thesis [in Russian], Sverdlovsk (1969).
O. Dimroth, Ber., 40, 2402 (1907).
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See [1] for communication XXX.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 831–835, June, 1971.
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Lipunova, G.N., Motyleva, E.P. & Bednyagina, N.P. Studies in the benz- and naphthazole series. Chem Heterocycl Compd 7, 776–780 (1971). https://doi.org/10.1007/BF00476832
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DOI: https://doi.org/10.1007/BF00476832