Cyclocondensation of 2-Hydroxyimino-1-(naphthalen-1-yl)butane-1,3-dione with Alkyl Hydrazines Leading to Substituted 4-Nitrosopyrazoles

Описание

Тип публикации: статья из журнала

Год издания: 2020

Идентификатор DOI: 10.1002/slct.202002574

Ключевые слова: nitrogen heterocycles, nitrosopyrazole, nmr spectroscopy, quantum chemical calculations, x-ray powder diffraction analysis

Аннотация: Cyclocondensation of 2-(hydroxyimino)-1-(naphthalen-1-yl)butane-1,3-dione with alkyl hydrazines leading to new 1-alkyl-3(5)-methyl-5(3)-(naphthalene-1-yl)-4-nitrosopyrazoles is described. 8 previously unknown N-alkyl-4-nitrosopyrazoles with a 1-naphthalene substituent at the 3 or 5 position of the pyrazole ring were obtained as a rПоказать полностьюesult. It was found that yields of naphthyl-substituted pyrazoles with N-alkyl groups near the naphthalene substituent were significantly lower than for 3-(naphthalen-1-yl)-substituted pyrazoles. Particular yields of pairwise formed isomeric nitrosopyrazoles were associated with the different electrophilicity of the two carbonyl groups of the initial diketone. Using quantum chemical calculations by the DFT method B3LYP−D3/6-311G(d,p), the potential energies of the various conformers were estimated to draw a conclusion about the preferred attack of alkyl hydrazine on the carbonyl group, associated with the naphthalene ring. 1H NMR and 2D 1H-13C HSQC spectra of the compounds confirmed this direction of the reaction. The crystal structures of the synthesized compounds were established by X-ray powder diffraction technique. Crystal structure data were in agreement with quantum chemical calculations. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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Издание

Журнал: ChemistrySelect

Выпуск журнала: Vol. 5, Is. 27

Номера страниц: 8289-8294

ISSN журнала: 23656549

Авторы

  • Bobrov Pavel S. (Reshetnev Siberian State Univ Sci & Technol, Dept Organ Chem & Technol Organ Subst, 31 Krasnoyarskii Rabochii Prospekt, Krasnoyarsk 660037, Russia)
  • Kirik Sergei D. (Siberian Fed Univ, Dept Inorgan & Phys Chem, 79 Svobodny Av, Krasnoyarsk 660041, Russia)
  • Krasnov Pavel O. (Siberian Fed Univ, Lab Nonlinear Opt & Spect, 79 Svobodny Av, Krasnoyarsk 660041, Russia; Reshetnev Siberian State Univ Sci & Technol, Dept Tech Phys, 31 Krasnoyarskii Rabochii Prospekt, Krasnoyarsk 660037, Russia)
  • Lyubyashkin Aleksey V. (Reshetnev Siberian State Univ Sci & Technol, Dept Organ Chem & Technol Organ Subst, 31 Krasnoyarskii Rabochii Prospekt, Krasnoyarsk 660037, Russia)
  • Suboch Georgiy A. (Reshetnev Siberian State Univ Sci & Technol, Dept Organ Chem & Technol Organ Subst, 31 Krasnoyarskii Rabochii Prospekt, Krasnoyarsk 660037, Russia)
  • Tovbis Mikhail S. (Reshetnev Siberian State Univ Sci & Technol, Dept Organ Chem & Technol Organ Subst, 31 Krasnoyarskii Rabochii Prospekt, Krasnoyarsk 660037, Russia)

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