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New derivatives of 4,5-dihydro-1H-pyrazole, 4,5-dihydro-1,2-oxazole, and pyrimidine prepared proceeding from (E)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-one

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Abstract

Condensation of acetylferrocene with 5-phenyl(4-methylphenyl)-1,2-oxazole-3-carbaldehydes afforded (Е)-3-[5-phenyl(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-ones. Reactions of (Е)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-one with semicarbazide, thiosemicarbazide, and hydroxylamine led to the formation of 5-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-3-ferrocenyl-4,5-dihydro-1H-pyrazole- 1-carboxamide, 5-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-3-ferrocenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide, and 5-(4-methylphenyl)-3'-ferrocenyl-4',5'-dihydro-3,5'-bi-1,2-oxazole respectively. Reactions of (Е)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-one with guanidine and thiourea result in 4-[5-(4-methyl-phenyl)-1,2-oxazol-3-yl]-6-ferrocenylpyrimidin-2-amine and -2-thione respectively.

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072, Belarus

    V. I. Potkin, S. K. Petkevich, A. V. Kletskov, I. A. Kolesnik, T. D. Zvereva & N. A. Zhukovskaya

  2. Favorskii Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, Russia

    G. G. Levkovskaya & I. B. Rozentsveig

Authors
  1. V. I. Potkin
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  2. S. K. Petkevich
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  3. A. V. Kletskov
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  4. I. A. Kolesnik
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  5. T. D. Zvereva
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  6. N. A. Zhukovskaya
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  7. G. G. Levkovskaya
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  8. I. B. Rozentsveig
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Correspondence to V. I. Potkin.

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Original Russian Text © V.I. Potkin, S.K. Petkevich, A.V. Kletskov, I.A. Kolesnik, T.D. Zvereva, N.A. Zhukovskaya, G.G. Levkovskaya, I.B. Rozentsveig, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 2, pp. 246–250.

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Potkin, V.I., Petkevich, S.K., Kletskov, A.V. et al. New derivatives of 4,5-dihydro-1H-pyrazole, 4,5-dihydro-1,2-oxazole, and pyrimidine prepared proceeding from (E)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-one. Russ J Org Chem 53, 240–245 (2017). https://doi.org/10.1134/S1070428017020178

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  • DOI: https://doi.org/10.1134/S1070428017020178

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