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Synthesis of 2-Aryl-4-(R-sulfanylmethyl)-3-methyl-6,7-dihydro-2H-pyrazolo[3,4-d]pyridazin-7-ones

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Abstract

Bromination of ethyl 1-aryl-4-acetyl-5-methyl-1H-pyrazole-3-carboxylates gave ethyl 1-aryl-4-(bromoacetyl)-5-methyl-1H-pyrazol-3-carboxylates which were used to alkylate benzenethiol and heterocyclic thiones at the sulfur atom. Reactions of the resulting S-alkylation products with hydrazine or methylhydrazine involved closure of pyridazine ring to afford 2-aryl-3-methyl-4-[phenyl(or hetaryl)sulfanylmethyl]-6,7-dihydro-2H-pyrazolo[3,4-d]pyridazin-7-ones.

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References

  1. Matiichuk, V.S., Potopnyk, M.A., and Obushak, N.D., Russ. J. Org. Chem., 2009, vol. 45, p. 712.

    CAS  Google Scholar 

  2. Matiichuk, V.S., Potopnyk, M.A., and Obushak, N.D., Russ. J. Org. Chem., 2008, vol. 44, p. 1352.

    Article  CAS  Google Scholar 

  3. Al-Zaydi, K.M. and Hafez, E.A.A., J. Chem. Res., Miniprint, 1999, p. 1621.

  4. Carpino, P.A. and Dow, R.L., WO Patent no. 111849, 2006.

  5. Carpino, P.A. and Sakya, S.M., WO Patent no. [vn61504}, 2005.

  6. Bildirici, I., Şener, A., Atalan, E., Battal, A., and Genz, H., Med. Chem. Res. 2009, vol. 18, p. 327.

    Article  CAS  Google Scholar 

  7. Chang, E.-M., Lin, C.-J., Wong, F.F, and Yeh, M.-Y., Heterocycles, 2006, vol. 68, p. 733.

    Article  CAS  Google Scholar 

  8. Erian, A.W., Sherif, M.S., and Gaber, H.M., Molecules, 2003, vol. 8, p. 793.

    Article  CAS  Google Scholar 

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Correspondence to N. D. Obushak.

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Original Russian Text © V.S. Matiichuk, M.A. Potopnyk, N.D. Obushak, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 10, pp. 1544–1551.

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Matiichuk, V.S., Potopnyk, M.A. & Obushak, N.D. Synthesis of 2-Aryl-4-(R-sulfanylmethyl)-3-methyl-6,7-dihydro-2H-pyrazolo[3,4-d]pyridazin-7-ones. Russ J Org Chem 46, 1550–1557 (2010). https://doi.org/10.1134/S1070428010100192

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  • DOI: https://doi.org/10.1134/S1070428010100192

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