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

Игорь Л. Далингер, Александр В. Корманов, Ирина А. Вацадзе, Татьяна К. Шкинева, Андрей М. Козеев, Борис Б. Аверкиев, Алексей Б. Шереметев
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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


Keywords


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

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