SYNTHESIS OF 1- AND 5-(PYRAZOLYL)TETRAZOLE AMINO AND NITRO DERIVATIVES

Authors

  • Игорь Л. Далингер N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Александр В. Корманов N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Ирина А. Вацадзе N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Ольга B. Серушкина N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Татьяна К. Шкинева N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Кирилл Ю. Супоницкий A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Acdemy of Sciences, 28 Vavilova St., Moscow 119991
  • Алла Н. Пивкина N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow 119991 National Research Nuclear University MEPhI, 31 Kashirskoe shosse, Moscow 115409
  • Шереметев А. Борисович N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991

DOI:

https://doi.org/10.1007/3513

Keywords:

nitropyrazole, tetrazole, N-amination, multinuclear NMR, nitration, reduction, regioselectivity, X-ray structural analysis

Abstract

Regioselective introduction of nitro groups was studied in the case of pyrazoles containing a 1- or 5-tetrazole substituent at position 3(5). All the possible isomeric С-mononitropyrazoles were synthesized. The reduction of these compounds gave the respective 3(5)-amino-5(3)-tetrazolylpyrazoles, which were nitrated to 3(5)-nitramino-4-nitro-5(3)-tetrazolylpyrazoles. The reaction of 1-(nitropyrazol-3(5)-yl)tetrazoles with hydroxylamine-О-sulfonic acid produced the respective N-amino derivatives.

Authors: Igor L. Dalinger*, Alexandr V. Kormanov, Irina A. Vatsadze, Olga V. Serushkina, Tatyana K. Shkineva, Kyrill Yu. Suponitsky, Alla N. Pivkina, Aleksei B. Sheremetev

Author Biographies

Игорь Л. Далингер, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991

Игорь Львович Далингер

заведующий лабораторией, д.х.н.

Александр В. Корманов, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991

Александр Васильевич Корманов

ведущий инженер

Ирина А. Вацадзе, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991

Ирина Анатольевна Вацадзе м.н.с.

Ольга B. Серушкина, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991

Ольга Викторовна Серушкина м.н.с.

Татьяна К. Шкинева, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991

Татьяна Константиновна Шкинева н.с., к.х.н.

Кирилл Ю. Супоницкий, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Acdemy of Sciences, 28 Vavilova St., Moscow 119991

Кирилл Юрьевич Супоницкий

Алла Н. Пивкина, N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow 119991 National Research Nuclear University MEPhI, 31 Kashirskoe shosse, Moscow 115409

Алла Николаевна Пивкина

Шереметев А. Борисович, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991

Шереметев Алексей Борисович

вед.н.с., д.х.н.

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Published

2017-01-06

Issue

Vol. 52 No. 12 (2016)

Section

Original Papers