<i>N</i>-ALKYLATION AND <i>N</i>-AMINATION OF ISOMERIC NITRO DERIVATIVES OF 3-METHYL-4-(1<i>H</i>-PYRAZOL-3(5)-YL)FURAZAN

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
  • Татьяна К. Шкинева N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Андрей М. Козеев N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Борис Б. Аверкиев A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow 119991
  • Алексей Б. Шереметев N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991

DOI:

https://doi.org/10.1007/2631

Keywords:

furazan, nitropyrazole, N-acetonylation, N-amination, conformational analysis, multinuclear NMR, regioselectivity, X-ray structural study

Abstract

The reaction of bromoacetone and hydroxylamine-О-sulfonic acid with isomeric mono- and dinitropyrazoles containing a furazanyl moiety at position 3(5) gave pairs of regioisomeric products from pyrazole ring N-acetonylation and N-amination, respectively, that were characterized in detail by multinuclear NMR spectroscopy. X-ray structural study of the four synthesized N-amino derivatives indicated a non-planar structure, while the conformational analysis pointed to conformational lability of such molecules, and the role of intermolecular interactions in determining the crystal structure.

How to Cite
Dalinger, I. L.; Kormanov, A. V.; Vatsadze, I. A.; Shkineva, T. K.; Kozeev, A. M.; Averkiev, B. B.; Sheremetev, A. B. Chem. Heterocycl. Compd. 2015, 51, 819. [Khim. Geterotsikl. Soedin. 2015, 51, 819.]

For this article in the English edition see DOI 10.1007/s10593-015-1781-7

Author Biography

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

Алексей Борисович Шереметев

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Published

2015-10-13

Issue

Vol. 51 No. 9 (2015)

Section

Original Papers