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Synthesis of monomeric and oligomeric 1,1′-methylenebis-(1H-pyrazoles) contaning ethynyl fragments

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Abstract

1,1′-Methylenebis(1H-pyrazole) and 1,1′-methylenebis(3,5-dimethyl-1H-pyrazole) reacted with iodine in the presence of iodic acid to give the corresponding 4,4′-diiodo derivatives. Polycondensation of the latter with p-diethynylbenzene led to the formation of oligomeric compounds. 1,1′-Methylenebis(4-iodo-1H-pyrazoles) were converted into 4,4′-diethynyl derivatives by the Sonogashira and reverse Favorskii reactions, and their oxidative polycondensation in the presence of copper(I) chloride in pyridine also gave oligomeric products with a molecular weight exceeding 9000.

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References

  1. Pettinari, C. and Pettinari, R., Coord. Chem. Rev., 2005, vol. 249, p. 663.

    Article  CAS  Google Scholar 

  2. Pomogailo, A.D. and Uflyand, I.E., Ros. Khim. Zh., 1996, vol. 40, nos. 4–5, p. 55.

    CAS  Google Scholar 

  3. Merkushev, E.B., Synthesis, 1988, p. 923.

  4. Sonogashira, K., Tohda, Y., and Hagihara, N., Tetrahedron Lett., 1975, vol. 50, p. 4467; Sonogashira, K., J. Organomet. Chem., 2002, vol. 653, p. 46.

    Article  Google Scholar 

  5. Rusanov, A.L., Khotina, I.A., and Begretov, M.M., Usp. Khim., 1997, vol. 66, p. 1162.

    CAS  Google Scholar 

  6. Bunz, U., Chem. Rev., 2000, vol. 100, p. 1605.

    Article  CAS  Google Scholar 

  7. Kotlyarevskii, I.L., Shvartsberg, M.S., Vasilevskii, S.F., and Andrievskii, V.N., Izv. Akad. Nauk SSSR, Ser. Khim., 1966, p. 302.

  8. Vasilevskii, S.F. and Shvartsberg, M.S., Izv. Akad. Nauk SSSR, Ser. Khim., 1980, p. 1071.

  9. Shvartsberg, M.S., Ivanchikova, I.D., and Vasilevskii, S.F., Izv. Ross. Akad. Nauk, Ser. Khim., 1998, p. 2027.

  10. Ciana, D. and Haim, L., J. Heterocycl. Chem., 1984, vol. 21, p. 607.

    Article  Google Scholar 

  11. Byers, P., Canty, A., Honeyman, T., Claramunt, R., Lopez, C., Lavandera, J., and Elguero, J., Gazz. Chim. Ital., 1992, vol. 122, p. 341; Levy, G.C. and Nelson, G.L., Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, New York: Wiley, 1972. Translated under the title Rukovodstvo po yadernomu magnitnomu rezonansu ugleroda-13 dlya khimikov-organikov, Moscow: Mir, 1975, p. 125

    CAS  Google Scholar 

  12. Potapov, A.S. and Khlebnikov, A.I., Izv. Vyssh. Uchebn Zaved., Ser. Khim. Khim. Tekhnol., 2003, no. 7, p. 66.

  13. Physical Methods in Heterocyclic Chemistry, Katritzky, A.R., Ed., New York: Academic, 1963, p. 533.

    Google Scholar 

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Authors and Affiliations

  1. Polzunov Altai State Technical University, pr. Lenina 46, Barnaul, 656038, Russia

    A. S. Potapov & A. I. Khlebnikov

  2. Institute of Chemical Kinetics and Combustion, Siberian Division, Russian Academy of Sciences, Novosibirsk, Russia

    S. F. Vasilevskii

Authors
  1. A. S. Potapov
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  2. A. I. Khlebnikov
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  3. S. F. Vasilevskii
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Original Russian Text © A.S. Potapov, A. I. Khlebnikov, S.F. Vasilevskii, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 9, pp. 1384–1389.

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Potapov, A.S., Khlebnikov, A.I. & Vasilevskii, S.F. Synthesis of monomeric and oligomeric 1,1′-methylenebis-(1H-pyrazoles) contaning ethynyl fragments. Russ J Org Chem 42, 1368–1373 (2006). https://doi.org/10.1134/S107042800609020X

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  • DOI: https://doi.org/10.1134/S107042800609020X

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